132891-79-3

Basic information

• Product Name: 4-O-ACETYL-3,6-DI-O-(TERT-BUTYLDIMETHYLSILYL)-D-GLUCAL
• Synonyms: 4-O-ACETYL-3,6-DI-O-(TERT-BUTYLDIMETHYLSILYL)-D-GLUCAL
• CAS NO: 132891-79-3
• Molecular Formula: C₂₀H₄₀O₅Si₂
• Molecular Weight: 450.71
• Mol File: 132891-79-3.mol

Chemical Properties

• Boiling Point: 324 °C(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 0.968 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.456(lit.)
• CAS DataBase Reference: 4-O-ACETYL-3,6-DI-O-(TERT-BUTYLDIMETHYLSILYL)-D-GLUCAL(CAS DataBase Reference)
• NIST Chemistry Reference: 4-O-ACETYL-3,6-DI-O-(TERT-BUTYLDIMETHYLSILYL)-D-GLUCAL(132891-79-3)
• EPA Substance Registry System: 4-O-ACETYL-3,6-DI-O-(TERT-BUTYLDIMETHYLSILYL)-D-GLUCAL(132891-79-3)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 132891-79-3(Hazardous Substances Data)

Upstream product

• 108-24-7 acetic anhydride 
• 111830-53-6 1,2-dideoxy-3,6-di-O-tert-butyldimethylsilyl-2-deoxy-D-arabino-1-hexenopyranose 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 13265-84-4 D-glucal 

Downstream Products

• 1621188-38-2 methyl 2,3,4-tri-O-benzyl-6-O-(4-O-acetyl-2-deoxy-3,6-di-O-tert-butyldimethylsilyl-α-D-erythro-hexapyranosyl)-α-D-glucopyranoside 
• 1621188-39-3 methyl 2,3,4-tri-O-benzyl-6-O-(4-O-acetyl-2-deoxy-3,6-di-O-tert-butyldimethylsilyl-β-D-erythro-hexapyranosyl)-α-D-glucopyranoside 
• 132891-83-9 4-O-(2-Amino-2-deoxy-α-D-glucopyranosyl)-1-O-dihydrogenphosphoryl-D-myo-inositol 

Relevant articles and documents

A 3,4-trans-fused cyclic protecting group facilitates α-selective catalytic synthesis of 2-deoxyglycosides

A practical approach has been developed to convert glucals and rhamnals into disaccharides or glycoconjugates with high α-selectivity and yields (77-97 %) using a trans-fused cyclic 3,4-O-disiloxane protecting group and TsOH·H2O (1 mol %) as a catalyst. Control of the anomeric selectivity arises from conformational locking of the intermediate oxacarbenium cation. Glucals outperform rhamnals because the C6 side-chain conformation augments the selectivity.

Convenient preparations of 2,3-dihydro-4H-pyran-4-ones from D-glucal triacetate: Selective oxidations of allylic acetates and allylic silyl ethers using N-bromosuccinimide

N-Bromosuccinimide (1.1 eq) in the presence of potassium carbonate (2 eq) and a catalytic amount of dibenzoyl peroxide converts the allylic acetates and the allylic silyl ethers (O-TBDMS or O-SiEt3) of secondary allylic alcohols, derived from D-glucal 3a into corresponding dihydro γ-pyrones 2.

GLYCOSYL-INOSITOL DERIVATIVES III. SYNTHESIS OF HEXOSAMINE-INOSITOL-PHOSPHATES RELATED TO PUTATIVE INSULIN MEDIATORS

The disaccharides related to glycosyl phosphatidyl inositol anchors of membrane proteins, 4-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol-1-phosphate and 4-O-(2-amino-2-deoxy-α-D-galactopyranosyl)-D-chiro-inositol-1-phosphate, have been prepared from optically resolved myo-inositol derivatives.The chiro-inositol moiety was obtained by epimerization of a selectively blocked myo-inositol-triflate ester.The resolved inositols were subsequently phosphorylated to yield the disaccharide aglycones.The amino-sugar components were prepared by azidonitration of suitably protected glucal and galactal derivatives.The derived pyranosyl chlorides were then condensed with the inositol phosphates using silver triflate as the promoter.