(tert-Butyldimethylsilyloxy)acetaldehyde - ≥90% , CAS No.102191-92-4

CAS: 102191-92-4 Cat. No.: I131842 Molecular Weight: 174.31 EC Number: 629-471-6

GRADE & PURITY ≥90%

Synonyms

DTXSID40400520 | STL557021 | Acetaldehyde, [[(1,1-dimethylethyl)dimethylsilyl]oxy]- | B6269 | BP-31208 | tert-Butyldimethylsilyloxy)acetaldehyde | t-butyldimethylsiloxyacetaldehyde | BBL103211 | BS-19212 | SCHEMBL64584 | [tert-butyl(dimethyl)silyl]oxy}ace

Storage

Store at 2-8°C,Argon charged

Shipped In

Wet ice

Overview

(tert-Butyldimethylsilyloxy)acetaldehyde is used in tetrahydropyran subunit construction, yielding addition products in good amounts in various total syntheses of biologically active molecules.
Used in tetrahydropyran subunit construction.

Application：

(tert-Butyldimethylsilyloxy)acetaldehyde is a versatile reagent commonly used in synthetic glycobiology. It can act both as an aldol donor and an aldol acceptor in the stereocontrolled production of erythrose. It is used as an important reagent in the total synthesis of (+)-ambruticin, (−)-laulimalide, (−)-salinosporamide A, and (+)-leucascandrolide A.

Employed in the construction of the key tetrahydropyran subunit in a recent synthesis of the marine natural product (–)-dactylodide.

Specifications

Synonyms

DTXSID40400520 | STL557021 | Acetaldehyde, [[(1, 1-dimethylethyl)dimethylsilyl]oxy]- | B6269 | BP-31208 | tert-Butyldimethylsilyloxy)acetaldehyde | t-butyldimethylsiloxyacetaldehyde | BBL103211 | BS-19212 | SCHEMBL64584 | [tert-butyl(dimethyl)silyl]oxy}ace

Specifications & Purity

≥90%

Storage

Store at 2-8°C, Argon charged

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥90%

Names and Identifiers

• Pubchem Sid: 488194745
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488194745
• Canonical Smiles: CC(C)(C)[Si](C)(C)OCC=O
• IUPAC Name: 2-[tert-butyl(dimethyl)silyl]oxyacetaldehyde
• InChIKey: MEBFFOKESLAUSJ-UHFFFAOYSA-N
• INCHI: 1S/C8H18O2Si/c1-8(2,3)11(4,5)10-7-6-9/h6H,7H2,1-5H3
• Isomeric SMILES: CC(C)(C)[Si](C)(C)OCC=O
• WGK Germany: 3
• Molecular Weight: 174.31
• Reaxy-Rn: 3536465
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=3536465&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organometallic compounds
    • Class Organometalloid compounds
      • Subclass Organosilicon compounds
        • Level5 Organoheterosilanes
          • Level6 Trialkylheterosilanes

• Kingdom: Organic compounds
• Superclass: Organometallic compounds
• Class: Organometalloid compounds
• Subclass: Organosilicon compounds
• Intermediate Tree Nodes: Organoheterosilanes
• Direct Parent: Trialkylheterosilanes
• Alternative Parents: Silyl ethers Organic metalloid salts Organic oxides Hydrocarbon derivatives Aldehydes
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Trialkylheterosilane - Silyl ether - Organic metalloid salt - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organic salt - Organooxygen compound - Carbonyl group - Aldehyde - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as trialkylheterosilanes. These are organoheterosilanes, bearing a silicon atom linked to three alkyl groups and one heteroatom.
• 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

Chemical and Physical Properties

• Sensitivity: moisture & heat sensitive
• Refractive Index: n20/D 1.432 (lit.)
• Flash Point(°F): 140 °F
• Flash Point(°C): 60 °C
• Boil Point(°C): 65 °C/17 mmHg
• Molecular Weight: 174.310 g/mol
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 174.108 Da
• Monoisotopic Mass: 174.108 Da
• Topological Polar Surface Area: 26.300 Ų
• Heavy Atom Count: 11
• Formal Charge: 0
• Complexity: 136.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• 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

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