≥95% for sensitive chromatographic and analytical workflows requiring minimal baseline interference.
Store at 2-8°C Ships Wet ice Check lot-specific COA for exact specifications.
SDS, COA, datasheet, and spec sheet available for download. Lot-specific COA accessible via lot number lookup.
Cited in 0 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
9-(2',3',5'-Tri-O-benzyl-b-D-arabinofuranosyl)adenine is a nucleoside that has shown anticancer and antiviral properties. It inhibits replication of DNA and RNA in cells, which may be due to its ability to inhibit the synthesis of deoxyribonucleotides and ribonucleotides. This compound is synthetically produced from 2',3',5'-tri-O-benzyl b-D-arabinofuranosyl chloride and adenine monophosphate (AMP). 9-(2',3',5'-Tri-O-benzyl-b-D-arabinofuranosyl)adenine is also known as arabinoside A.
| Canonical Smiles | C1=CC=C(C=C1)COCC2C(C(C(O2)N3C=NC4=C(N=CN=C43)N)OCC5=CC=CC=C5)OCC6=CC=CC=C6 |
|---|---|
| IUPAC Name | 9-[(2R,3S,4R,5R)-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)oxolan-2-yl]purin-6-amine |
| InChIKey | WRFWNCVDEVBPJK-IIHCQYLKSA-N |
| INCHI | 1S/C31H31N5O4/c32-29-26-30(34-20-33-29)36(21-35-26)31-28(39-18-24-14-8-3-9-15-24)27(38-17-23-12-6-2-7-13-23)25(40-31)19-37-16-22-10-4-1-5-11-22/h1-15,20-21,25,27-28,31H,16-19H2,(H2,32,33,34)/t25-,27-,28+,31-/m1/s1 |
| Isomeric SMILES | C1=CC=C(C=C1)COC[C@@H]2[C@H]([C@@H]([C@@H](O2)N3C=NC4=C(N=CN=C43)N)OCC5=CC=CC=C5)OCC6=CC=CC=C6 |
| PubChem CID | 54445555 |
| Molecular Weight | 537.61 |
Comprehensive hazard, handling, storage, and regulatory compliance document.
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View spec sheet →Taxonomy Tree
| Kingdom | Organic compounds |
|---|---|
| Superclass | Nucleosides, nucleotides, and analogues |
| Class | Purine nucleosides |
| Subclass | Not available |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Purine nucleosides |
| Alternative Parents | Glycosylamines Pentoses 6-aminopurines Benzylethers Aminopyrimidines and derivatives N-substituted imidazoles Imidolactams Tetrahydrofurans Heteroaromatic compounds Oxacyclic compounds Dialkyl ethers Azacyclic compounds Primary amines Organopnictogen compounds Hydrocarbon derivatives |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Purine nucleoside - Glycosyl compound - N-glycosyl compound - 6-aminopurine - Pentose monosaccharide - Imidazopyrimidine - Benzylether - Purine - Aminopyrimidine - N-substituted imidazole - Monosaccharide - Monocyclic benzene moiety - Imidolactam - Benzenoid - Pyrimidine - Azole - Imidazole - Tetrahydrofuran - Heteroaromatic compound - Oxacycle - Dialkyl ether - Ether - Azacycle - Organoheterocyclic compound - Organic oxygen compound - Amine - Organic nitrogen compound - Hydrocarbon derivative - Organopnictogen compound - Primary amine - Organooxygen compound - Organonitrogen compound - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as purine nucleosides. These are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety. |
| External Descriptors | Not available |
Find and download the COA for your product by matching the lot number on the packaging.
| Lot Number | Certificate Type | Date | Item |
|---|---|---|---|
 G2518488 | Certificate of Analysis | Feb 13, 2025 | T345340 |
| G2518489 | Certificate of Analysis | Feb 13, 2025 | T345340 |
| G2518490 | Certificate of Analysis | Feb 13, 2025 | T345340 |
| G2518491 | Certificate of Analysis | Feb 13, 2025 | T345340 |
| G2518492 | Certificate of Analysis | Feb 13, 2025 | T345340 |
| G2518493 | Certificate of Analysis | Feb 13, 2025 | T345340 |
| Molecular Weight | 537.600 g/mol |
|---|---|
| XLogP3 | 3.700 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 8 |
| Rotatable Bond Count | 11 |
| Exact Mass | 537.238 Da |
| Monoisotopic Mass | 537.238 Da |
| Topological Polar Surface Area | 107.000 Ų |
| Heavy Atom Count | 40 |
| Formal Charge | 0 |
| Complexity | 745.000 |
| 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 |
