29868-42-6

Basic information

• Product Name: Methyl 2,3-di-O-acetyl-α-D-glucopyranoside
• Synonyms: Methyl 2,3-di-O-acetyl-α-D-glucopyranoside;(2S,3R,4S,5R,6R)-5-Hydroxy-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4-diyl diacetate
• CAS NO: 29868-42-6
• Molecular Weight: 278.259
• Mol File: 29868-42-6.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Methyl 2,3-di-O-acetyl-α-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 2,3-di-O-acetyl-α-D-glucopyranoside(29868-42-6)
• EPA Substance Registry System: Methyl 2,3-di-O-acetyl-α-D-glucopyranoside(29868-42-6)

Safety Data

• Hazardous Substances Data: 29868-42-6(Hazardous Substances Data)

Upstream product

• 108-24-7 acetic anhydride 
• 4056-12-6 methyl 4,6-O-(phenylborylene)-α-D-glucopyranoside 
• 944721-02-2 C₃₁H₂₇F₂₁O₈ 
• 944721-01-1 C₂₉H₂₇F₁₇O₈ 
• 944721-00-0 C₂₇H₂₇F₁₃O₈ 
• 2774-22-3 methyl 2,3-di-O-acetyl-4,6-O-benzylidene-α-D-glucopyraniside 
• 302783-17-1 methyl 2,3-di-O-acetyl-4,6-O-p-methoxybenzylidene-α-D-glucopyranoside 

Downstream Products

• 53717-00-3 methyl 2,3-di-O-acetyl-6-O-trityl-α-D-glucopyranoside 
• 29868-43-7 methyl 2,3-di-O-acetyl-6-O-benzoyl-α-D-glucopyranoside 
• 18031-51-1 methyl 2,3,6-tri-O-acetyl-α-D-glucopyranoside 
• 477949-33-0 Acetic acid (2S,3R,4S,5R,6R)-3-acetoxy-6-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-hydroxy-2-methoxy-tetrahydro-pyran-4-yl ester 
• 291774-70-4 methyl 2,3-di-O-acetyl-6-phenylthio-6-deoxy-α-D-glucopyranoside 
• 1381876-05-6 methyl 2,3-di-O-acetyl-4,6-di-O-tert-butyldiphenylsilyl-α-D-mannopyranoside 
• 1381876-07-8 methyl 2,3-di-O-acetyl-α-D-mannopyranoside 
• 1381875-92-8 methyl 2,3-di-O-acetyl-4-O-pivaloyl-6-O-tert-butyldiphenylsilyl-α-D-mannopyranoside 

Relevant articles and documents

Highly Regioselective Monoacylation of Unprotected Glucopyranoside Using Transient Directing-Protecting Groups

The regioselective functionalization of monosaccharides is notoriously achieved using metal catalysis, lengthy synthetic strategies requiring protection/deprotection, various enzymes, or other methods that target cis-diols (and thus cannot be used with glucopyranose derivatives), In this paper, we report a new method using selected boronic acids as temporary protecting groups, and describe its application to the regioselective functionalization of methyl α-d-glucopyranoside, the most difficult monosaccharide to functionalize regioselectively. Generally, reactions of glucopyranosides may lead to a plethora of mono- and polyfunctionalized derivatives, yet our method gave the 3-O-acetylated, 2-O-benzoylated, and 2-O-pivaloylated derivatives of methyl α-d-glucopyranoside as major products. We focused on the use of recyclable and green temporary protecting groups (in a one-pot reaction) and on the modulation of the intramolecular hydrogen-bonding network using selected arylboronic acids. A complete scalable procedure leading to a single regioisomer from unprotected methyl α-d-glucopyranoside is presented.

Facile chelation-controlled reductive opening of methoxybenzylidene acetals with Bu3SnH and MgBr2. Regioselective protection strategy as MPM ethers

A mild and efficient regioselective reductive opening of methoxybenzylidene acetals using a combination of Bu3SnH and MgBr2·OEt2, mainly via five-membered chelation intermediates is described. This reaction was applied to synthetic intermediates of myriaporon and tedanolide. (C) 2000 Elsevier Science Ltd.