DMT-OMe-rA(Bz) - Suitable for molecular biology, ≥98% , CAS No.110764-72-2

CAS: 110764-72-2 Cat. No.: N692253 Summenformel: C₃₉H₃₇N₅O₇ Molekulargewicht: 687.75

GRADE & PURITY Suitable for molecular biology, ≥98%

Synonyms

N-(9-((2R,3R,4R,5R)-5-((Bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-hydroxy-3-methoxytetrahydrofuran-2-yl)-9H-purin-6-yl)benzamide | 5'-O-DMTr-2'-O-Me-rA(Bz); N6-Bz-DMT-2'-OMe-Ar

Storage

Store at 2-8°C,Protected from light,Argon charged

Shipped In

Wet ice

Übersicht

DMT-OMe-rA(Bz) is a nucleoside analog.

Specifications

Synonyme

N-(9-((2R,3R,4R,5R)-5-((Bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-hydroxy-3-methoxytetrahydrofuran-2-yl)-9H-purin-6-yl)benzamide | 5'-O-DMTr-2'-O-Me-rA(Bz); N6-Bz-DMT-2'-OMe-Ar

Spezifikationen & Reinheit

Suitable for molecular biology, ≥98%

Stabilität und Lagerung

Store at -2-8 ℃ (24 months). Under Inert Atmosphere. Store in the dark.

Storage

Store at 2-8°C,Protected from light,Argon charged

Verschickt in

Wet ice

Dieses Produkt erfordert Kühlkettenversand. Grundversand und andere Economy-Optionen sind nicht verfügbar.

Note

Suitable for molecular biology

Reinheit

≥98%

Namen und Kennungen

Kanonisches Lächeln

COC1C(C(OC1N2C=NC3=C(N=CN=C32)NC(=O)C4=CC=CC=C4)COC(C5=CC=CC=C5)(C6=CC=C(C=C6)OC)C7=CC=C(C=C7)OC)O

IUPAC Name

N-[9-[(2R,3R,4R,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-hydroxy-3-methoxyoxolan-2-yl]purin-6-yl]benzamide

InChIKey

SARHDAQOZNKZCC-CJEGOSRCSA-N

INCHI

1S/C39H37N5O7/c1-47-29-18-14-27(15-19-29)39(26-12-8-5-9-13-26,28-16-20-30(48-2)21-17-28)50-22-31-33(45)34(49-3)38(51-31)44-24-42-32-35(40-23-41-36(32)44)43-37(46)25-10-6-4-7-11-25/h4-21,23-24,31,33-34,38,45H,22H2,1-3H3,(H,40,41,43,46)/t31-,33-,34-,38-/m1/s1

Isomere SMILES

CO[C@@H]1[C@@H]([C@H](O[C@H]1N2C=NC3=C(N=CN=C32)NC(=O)C4=CC=CC=C4)COC(C5=CC=CC=C5)(C6=CC=C(C=C6)OC)C7=CC=C(C=C7)OC)O

Molekulargewicht

687.75

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Klasse Triphenyl compounds

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Klasse: Triphenyl compounds
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Triphenyl compounds
• Alternative Parents: Purine nucleosides Glycosylamines Pentoses Benzamides Purines and purine derivatives Benzylethers Anisoles Phenoxy compounds Benzoyl derivatives Methoxybenzenes Alkyl aryl ethers Pyrimidines and pyrimidine derivatives Imidolactams N-substituted imidazoles Heteroaromatic compounds Oxolanes Secondary carboxylic acid amides Secondary alcohols Dialkyl ethers Oxacyclic compounds Azacyclic compounds Hydrocarbon derivatives Organonitrogen compounds Organic oxides
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Triphenyl compound - Purine nucleoside - N-glycosyl compound - Glycosyl compound - Pentose monosaccharide - Benzylether - Purine - Imidazopyrimidine - Benzoic acid or derivatives - Benzamide - Benzoyl - Methoxybenzene - Phenol ether - Anisole - Phenoxy compound - Alkyl aryl ether - Imidolactam - Monosaccharide - Pyrimidine - N-substituted imidazole - Monocyclic benzene moiety - Azole - Heteroaromatic compound - Imidazole - Oxolane - Secondary alcohol - Secondary carboxylic acid amide - Carboxamide group - Oxacycle - Azacycle - Organoheterocyclic compound - Carboxylic acid derivative - Dialkyl ether - Ether - Organic nitrogen compound - Alcohol - Organic oxygen compound - Organooxygen compound - Organonitrogen compound - Organic oxide - Hydrocarbon derivative - Aromatic heteropolycyclic compound
• Beschreibung: This compound belongs to the class of organic compounds known as triphenyl compounds. These are aromatic compounds containing a triphenyl moiety.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemische und physikalische Eigenschaften

• Empfindlichkeit: Light & Moisture & Air sensitive
• Molekulargewicht: 687.700 g/mol
• XLogP3: 5.000
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 12
• Exact Mass: 687.269 Da
• Monoisotopic Mass: 687.269 Da
• Topological Polar Surface Area: 139.000 Ų
• Heavy Atom Count: 51
• Formal Charge: 0
• Complexity: 1070.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 4
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Application Protocols

No item‑specific, validated application protocols are provided in the Product Data for this SKU. For general guidance (literature/general):

• Preparing a 3′‑O‑phosphoramidite from DMT‑OMe‑rA(Bz): Dry the nucleoside (vacuum, P2O5 or co‑evaporation with dry MeCN), dissolve in anhydrous MeCN/DCM under argon, add DIPEA followed by 2‑cyanoethyl N,N‑diisopropylchlorophosphoramidite at 0–5 °C, warm to RT, monitor by TLC/LC–MS, then work up under low‑acid conditions.
• Making stock solutions (post‑phosphitylation): Dissolve the amidite at ~0.1 M in anhydrous MeCN, sparge with argon, store over 3 Å sieves in sealed amber vials at 2–8 °C for short term. Validate stability before automated runs.
• Solid‑phase synthesis (overview): Use standard RNA synthesis cycles with ETT activation, brief detritylation in DCM/TCA, iodine oxidation, and final base deprotection/cleavage. Adjust coupling times for challenging sequences.

Please consult Aladdin Scientific’s SDS and your instrument manufacturer’s guidelines. For detailed, lot‑specific parameters (water content limits, purity, residual solvents), refer to the CoA/Spec Sheet.

Biological Roles

General biochemical context (literature/general)

• Adenosine is a canonical ribonucleoside participating in RNA structure and numerous biochemical processes. The 2′‑O‑methyl modification is a naturally occurring ribose methylation found in rRNA, tRNA, snRNA, and some mRNA cap structures (Am), influencing RNA folding, stability, and interactions with proteins.
• Functional consequences of 2′‑O‑methylation:
  • Increases resistance to nuclease cleavage by stabilizing the C3′‑endo sugar pucker and reducing in‑line transesterification propensity.
  • Modulates thermodynamics of base pairing, often slightly increasing duplex Tm in A‑form helices.
  • Affects recognition by RNA‑binding proteins and enzymes; in innate immune sensing, 2′‑O‑methylation can alter pattern recognition of RNA compared to unmodified counterparts (mechanistic, non‑clinical note).
• Protection strategy relevance:
  • N6‑benzoyl mimics the neutralization of exocyclic amines used in biosynthesis to prevent side reactions; 5′‑DMT is a synthetic handle with no biological analog but facilitates stepwise chain assembly and purification.

Use of DMT‑OMe‑rA(Bz) in research

• Serves as a precursor to build site‑specific 2′‑O‑methylated adenosine residues within synthetic RNAs for structure–function studies, ribozyme engineering, or as controls in analytical assays of RNA modification mapping. No medical or clinical use is implied.

Buffer Applications

This product is a protected nucleoside building block rather than a buffering agent. It does not form a defined conjugate acid/base pair suitable for pH control, and it is poorly soluble in water due to its protecting groups. For aqueous buffer needs in oligonucleotide workflows, use standard systems (e.g., TE, phosphate, HEPES) prepared separately. Focus instead on the organic solvent guidance and synthesis protocols provided in the applicable sections above.

Green Alternatives

Context

• Traditional oligonucleotide chemistry relies on MeCN, DCM/DCE, and chlorophosphoramidite reagents, which pose environmental, health, and safety concerns. While DMT‑OMe‑rA(Bz) is inherently designed for these workflows, greener choices can be made around solvent and reagent selection (literature/general).

Greener options and tradeoffs (general)

• Solvent substitution for DCM in detritylation/extraction:
  • 2‑MeTHF or CPME can sometimes replace DCM for workups and certain detritylation protocols; however, trityl cation stability and optical monitoring may differ, and water content control is critical.
• High‑purity MeCN alternatives:
  • Bio‑sourced MeCN is increasingly available; still, MeCN remains favored for kinetics and solubility. Propylene carbonate has been explored but is often too viscous for automated dosing.
• Activators and oxidants:
  • Consider less hazardous activators (e.g., ETT versus older tetrazoles) and aqueous iodine alternatives where compatible. Validate on small scale before process changes.

Compact comparison (general; not item specifications)

• Detritylation solvent: DCM (benchmark) vs 2‑MeTHF (greener) — DCM offers fast kinetics and easy optical monitoring; 2‑MeTHF reduces chlorinated emissions but may require protocol re‑optimization.
• Workup solvent: EtOAc/2‑MeTHF over DCM to cut halogenated waste, with attention to solubility of DMT derivatives.

Best practices

• Implement solvent recycling for MeCN/DCM, use molecular sieves instead of azeotropic drying where feasible, and apply closed‑loop delivery to minimize emissions and exposure.

Pharmaceutical Uses

Role in pharmaceutical R&D and manufacturing (general, non‑clinical)

• Oligonucleotide starting material: DMT‑OMe‑rA(Bz) is a protection‑patterned nucleoside used to prepare 3′‑phosphoramidite monomers for solid‑phase synthesis of research‑grade and process‑development‑stage oligonucleotides incorporating 2′‑O‑methyl adenosine.
• Process considerations: The protection scheme (DMT/N6‑Bz/2′‑O‑Me) aligns with widely adopted deprotection and purification trains, facilitating method transfer between labs and scale‑up units.
• Regulatory context: There is no pharmacopeial monograph specific to this protected nucleoside. Any use in GMP settings would require supplier qualification, full specification/CoA review, impurity and residual solvent controls, and validated analytical methods. Item‑specific pharmacopeial or excipient status is Not specified for this item; refer to CoA/Spec Sheet.
• Formulation/excipient use: Not intended as an excipient; its role is as a reactive intermediate or starting material upstream of drug substance manufacturing for oligonucleotides.

Note: Aladdin Scientific supplies this material for research use only, as indicated in the Product Data. No therapeutic claims are made or implied.

Physical Properties

Item‑specific physical data

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
• Melting point, boiling point, density, refractive index, water/peroxide/metal limits, UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.

Typical properties for DMT‑protected 2′‑O‑methyl nucleosides (literature/general — not item specifications)

• Physical state: Usually a pale solid (foam or powder) due to the bulky DMT/Bz aromatic groups.
• Solubility: Good in dry aprotic organic solvents such as acetonitrile (MeCN), dichloromethane (DCM), dichloroethane, THF, and DMF; sparing in alcohols; essentially insoluble in water because of the lipophilic DMT and benzoyl groups.
• Polarity/lipophilicity: Significantly more lipophilic than unprotected adenosine; designed for compatibility with anhydrous, non‑protic synthesis media.
• UV characteristics: Strong absorbance in UV due to adenine and DMT chromophores; DMT+ cation has distinctive orange color enabling trityl monitoring during acid detritylation (qualitative, literature/general).

Handling sensitivity (from Product Data and general)

• The listing specifies “Store at 2–8 °C, protected from light, argon charged,” consistent with sensitivity to acid/moisture and photolability of DMT. Avoid prolonged exposure to acids or moisture that trigger detritylation/hydrolysis (literature/general).

Quality and Grades

Item‑specific grade

• Grade/Purity: Suitable for molecular biology (from Product Data).

What “Suitable for molecular biology” typically implies (general guidance)

• Low bioburden and nuclease‑free handling: Minimization of DNase/RNase/Protease contamination during manufacture and packaging, supporting use in workflows where nucleic acid integrity matters (e.g., oligonucleotide synthesis, enzymatic manipulations). Note: actual nuclease testing parameters and limits are Not specified for this item; refer to CoA/Spec Sheet.
• High chemical purity: Typically high assay purity with tightly controlled residual solvents and byproducts to support efficient downstream reactions. Exact assay % and impurity profile are Not specified for this item; refer to CoA/Spec Sheet.
• Trace metals/UV specs: Not specified for this item; refer to CoA/Spec Sheet.

Protecting group integrity

• DMT at 5′ is acid‑labile and serves as a chromophoric handle for trityl monitoring; N6‑benzoyl is base‑labile but stable during standard coupling; 2′‑O‑Me is non‑labile under typical synthesis conditions (literature/general).

Fit for purpose

• This protection pattern is widely used to prepare 3′‑phosphoramidites for automated RNA/2′‑O‑methyl oligonucleotide assembly. If you require enhanced specifications (e.g., HPLC‑grade residual UV background, water content by KF), request the CoA for the specific lot or contact Aladdin Scientific for a tighter spec package.

Reaction and Applications

Primary application domain (general for this compound type)

• Protected nucleoside precursor for the synthesis of 3′‑O‑phosphoramidite monomers used in automated assembly of RNA and 2′‑O‑methyl RNA oligonucleotides.

Functional roles of protecting groups (literature/general)

• 5′‑O‑DMT: Acid‑labile, enabling stepwise deprotection and trityl monitoring. Provides lipophilicity for chromatographic separations of intermediates.
• N6‑Benzoyl (A): Base‑labile, masks exocyclic amine during coupling; removed in final deprotection with ammonia or methylamine.
• 2′‑O‑Methyl: Permanent modification that enhances nuclease resistance and duplex stability in many sequence contexts; remains intact through standard synthesis/deprotection.

Representative workflows (general)

• Phosphitylation: Convert the 3′‑OH to the corresponding 2‑cyanoethyl N,N‑diisopropyl phosphoramidite using 2‑cyanoethyl N,N‑diisopropylchlorophosphoramidite and a hindered base (DIPEA) in anhydrous MeCN/DCM at 0–25 °C.
• Solid‑phase synthesis: The resulting amidite is dissolved in dry MeCN (typically ~0.1 M) and used on DNA/RNA synthesizers with ETT/Tetrazole activators for coupling. DMT detritylation monitored optically in DCM/TCA.
• Post‑synthesis deprotection: Cleavage from support and removal of Bz with ammonium hydroxide or AMA; 2′‑O‑Me remains.

Additional uses (general)

• Preparation of mixed‑backbone oligos (chimeric DNA/2′‑O‑Me RNA), and as a standard for analytical method development (HPLC/LC–MS) involving DMT cation monitoring.

Reaction Conditions

General conditions from literature for this compound class (guidance; not item specifications)

1. 3′‑O‑Phosphitylation to amidite

• Reagents: 2‑cyanoethyl N,N‑diisopropylchlorophosphoramidite (1.2–1.5 eq), DIPEA (2–3 eq) or Hunig’s base; optional catalytic DMAP.
• Solvent: Anhydrous MeCN/DCM (0.05–0.2 M).
• Temperature/time: 0–25 °C, 0.5–2 h under inert gas.
• Workup: Quench with mild base, aqueous wash, and silica gel chromatography under low‑acid conditions (avoid exposing to protic acid that cleaves DMT). Typical isolated yields reported for analogous substrates: 70–90%.

2. 5′‑Detritylation (analytical/preparative)

• Reagent: 2–3% trichloroacetic acid in DCM.
• Temperature/time: 0–25 °C, seconds to minutes until completion by TLC/UV (appearance of orange trityl cation).
• Quench: Pyridine or rapid filtration/washing to remove acid; immediately neutralize to avoid side reactions.

3. Solid‑phase coupling (using the derived amidite)

• Activator: ETT (0.25–0.5 M in MeCN) or 5‑ethylthio‑1H‑tetrazole; coupling times 1–5 min.
• Oxidation: I2 in water/THF/pyridine; sulfurization alternatives for phosphorothioates (e.g., PADS, DDTT).
• Deprotection/cleavage: NH3 or AMA; conditions depend on backbone and protecting groups.

Note: Rigorous solvent drying (<50–100 ppm H2O) and inert atmosphere handling are critical. Optimize per instrument and sequence context.

Safety and Handling

GHS classification and hazard statements

• Signal word: Not specified for this item; refer to SDS.
• Hazard statements (H‑codes): Not specified for this item; refer to SDS.
• Pictograms and GHS classification: Not specified for this item; refer to SDS.

General safety guidance for protected nucleosides (literature/general)

• Potential hazards: Organic solid with aromatic protecting groups; dust may be irritating. Not for human or animal use. For research use only.
• PPE: Use laboratory coat, safety glasses, and appropriate chemically resistant gloves (e.g., nitrile). Handle powders in a fume hood to minimize dust inhalation.
• Incompatibilities: Strong acids (promote rapid DMT detritylation), strong bases over extended times (risk of premature Bz removal), oxidants, and moisture. Avoid prolonged light exposure to protect DMT chromophore.
• Inert atmosphere: Product Data specifies argon charge; maintain under dry inert gas during transfers and solution preparation.
• First aid (overview; consult SDS): If inhaled, move to fresh air; if on skin/eyes, rinse with water for at least 15 minutes; if ingested, rinse mouth and seek medical attention. Show SDS to physician.
• Fire safety: Combustible organic solid. Use CO2, dry chemical, or foam. Thermal decomposition may form oxides of carbon and nitrogen; firefighters wear SCBA.
• Spill response: Avoid dust generation; collect mechanically or with damp disposable towels/HEPA vacuum; dispose according to local regulations.

Authoritative reference: Always consult the Aladdin Scientific SDS for this specific SKU for definitive hazard, exposure limits, and response procedures.

Solvent Selection

Solubility and compatibility (literature/general for this class)

• Preferred anhydrous solvents: Acetonitrile (MeCN), dichloromethane (DCM), 1,2‑dichloroethane (DCE), tetrahydrofuran (THF), and dimethylformamide (DMF). These enable moisture‑free handling and are standard in nucleoside protection/phosphitylation chemistry.
• Water/alcohols: Poor aqueous solubility due to DMT/Bz groups; protic solvents risk partial detritylation or benzoyl exchange under acidic/basic conditions.
• Dielectric/polarity: MeCN offers high polarity with low nucleophilicity, enabling fast phosphitylation and clean workups. DCM/DCE provide low polarity and rapid trityl precipitation/monitoring.

When to choose what (general)

• MeCN: Default for phosphitylation, amidite dissolution, and automated synthesis feeds because of low viscosity and favorable kinetics.
• DCM/DCE: Useful for detritylation steps (e.g., 2–3% TCA in DCM) and for extraction or crystallization of lipophilic DMT‑bearing intermediates.
• THF: Alternative medium for base‑sensitive operations; ensure rigorous drying (molecular sieves) and peroxide testing where applicable.
• DMF: For acylation or benzoylation steps requiring higher polarity/solvation power; minimize water content.

Practical tips (general)

• Drying: Pre‑dry solvents (e.g., 3 Å sieves for MeCN/DCM) to <50 ppm water when possible; exact water limits are Not specified for this item.
• Atmosphere: Maintain inert gas blanket (argon/nitrogen) to minimize adventitious moisture and acid traces that promote DMT loss (aligned with Product Data storage under argon).

Storage and Reconstitution

Item‑specific storage and shipping (from Product Data)

• Storage conditions: Store at 2–8 °C, protected from light, argon charged.
• Shipped on: Wet ice.
• Research use note: For research use only.

General best practices for this class

• Container: Keep in tightly sealed, moisture‑free, amber glass vials under inert gas. The argon charge noted in the Product Data should be maintained upon first opening by re‑blanketing with dry argon or nitrogen.
• Handling: Allow vial to equilibrate to room temperature before opening to prevent moisture condensation. Minimize time open to air; promptly recap and re‑purge.
• Short‑term solution preparation: For immediate synthetic use, dissolve in anhydrous acetonitrile, DCM, or DMF under inert atmosphere. Filter through PTFE (0.2 µm) if needed to remove particulates.
• Concentration guidance: If converted to the phosphoramidite, typical working solutions are ~0.1 M in dry MeCN for automated synthesis (literature/general). For the nucleoside precursor itself, prepare solutions as required for derivatization assays; stability depends on solvent dryness and absence of acid.
• Freeze–thaw: Avoid repeated freeze–thaw of solutions; aliquot under inert gas. Store solids at 2–8 °C as specified; do not store with acid vapors to prevent inadvertent detritylation.

For any lot‑specific stability and retest period information, consult the CoA/Spec Sheet.

Structure and Identity

Brief description: DMT‑OMe‑rA(Bz) is a protected adenosine derivative designed as a nucleoside building block precursor for oligonucleotide chemistry (RNA/2′‑O‑Me systems). It features a 5′‑O‑dimethoxytrityl (DMT) group, a 2′‑O‑methyl modification on ribose, and an N6‑benzoyl protection on adenine.

Item‑specific facts (from Product Data)

• SKU: N692253
• Product name: DMT‑OMe‑rA(Bz)
• CAS: 110764‑72‑2
• PubChem CID: 10770884
• InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.

Structural features (general description for this class)

• Core: Adenosine (adenine base attached to β‑D‑ribofuranose).
• Sugar protection: 2′‑O‑methyl group on ribose increases hydrophobicity and nucleolytic stability (literature/general).
• Exocyclic amine protection: N6‑benzoyl (Bz) on adenine, base‑labile under ammonia/methylamine conditions (literature/general).
• 5′‑Hydroxyl protection: 4,4′‑dimethoxytrityl (DMT), acid‑labile for stepwise deprotection/monitoring during oligo assembly (literature/general).
• 3′‑Position: Typically free 3′‑OH in the nucleoside precursor, enabling subsequent phosphitylation to give the 3′‑O‑(2‑cyanoethyl N,N‑diisopropyl)phosphoramidite monomer (literature/general).

2D structure in words (general)

• Purine ring (adenine) bearing an N6‑benzoyl substituent, attached via N9 to a ribofuranose ring. The ribose carries a DMT ether at the 5′‑oxygen, a methoxy substituent at the 2′‑oxygen, a free 3′‑OH (in the precursor), and a standard 1′‑β‑glycosidic linkage to the base.

Synthetic Utility

Functional group inventory (general)

• 5′‑O‑DMT ether: Acid‑labile protecting group; enables trityl cation colorimetric monitoring; increases hydrophobicity for separations.
• 2′‑O‑Methyl ether: Non‑labile under standard acid/base synthesis conditions; permanent RNA modification.
• N6‑Benzoyl amide: Base‑labile protecting group for adenine exocyclic amine; stable to brief acids and neutral coupling conditions.
• 3′‑OH (in precursor): Nucleophile for phosphitylation or other derivatizations.

Key transformations (literature/general)

• Phosphitylation: 3′‑O‑phosphoramidite formation with 2‑cyanoethyl N,N‑diisopropylchlorophosphoramidite/DIPEA in dry MeCN/DCM, furnishing the standard amidite monomer for automated synthesis.
• Alternative 3′‑derivatives: 3′‑H‑phosphonate formation (PCl3 route) or 3′‑phosphate introduction for enzymatic studies.
• Detritylation: Short exposure to 2–3% TCA in DCM selectively removes 5′‑DMT without affecting 2′‑O‑Me or N6‑Bz.
• N6‑deprotection: NH3 or AMA removes benzoyl after chain assembly and support cleavage.

Retrosynthetic value (general)

• The protection pattern orthogonalizes 5′ vs N6 vs 2′ positions, enabling convergent assembly of complex, site‑specifically modified RNAs and chimeras. The DMT handle streamlines purification (normal‑phase silica or RP‑HPLC via trityl‑on/off strategies) and analytical tracking by UV/vis or LC–MS (trityl signature).

Target Specificity

Not applicable. This product is a small‑molecule nucleoside building block rather than a biological targeting reagent (e.g., antibody, enzyme inhibitor, probe with defined biomolecular affinity). It has no item‑specific antigen/epitope or species reactivity attributes. See “Reaction & Applications” and “Synthetic Utility” for relevant use information.