51295-60-4

Basic information

• Product Name: methyl 3,4,6-tri-O-acetyl-α-D-glucopyranoside
• Synonyms: methyl 3,4,6-tri-O-acetyl-α-D-glucopyranoside
• CAS NO: 51295-60-4
• Molecular Weight: 320.296
• Mol File: 51295-60-4.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: methyl 3,4,6-tri-O-acetyl-α-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 3,4,6-tri-O-acetyl-α-D-glucopyranoside(51295-60-4)
• EPA Substance Registry System: methyl 3,4,6-tri-O-acetyl-α-D-glucopyranoside(51295-60-4)

Safety Data

• Hazardous Substances Data: 51295-60-4(Hazardous Substances Data)

Upstream product

• 108-24-7 acetic anhydride 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 3254-16-8 3,4,6-tri-O-acetyl-1,2-O-(1-methoxyethylidene)-β-D-mannopyranose 
• 27851-29-2 benzyl 2,3,4-tri-O-benzyl-D-glucopyranoside 
• 53008-65-4 methyl 2,3,4-tri-O-benzyl-D-glucopyranoside 
• 1197820-01-1 2-methoxy-2-(S)-phenyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-β-D-glucopyranoso)[1,2-e]-1,4-oxathiane (R)-S-oxide 
• 67-56-1 methanol 
• 604-69-3 β-D-glucose pentaacetate 
• 604-70-6 Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-methoxy-tetrahydro-pyran-4-yl ester 

Relevant articles and documents

Methyl 1,2-orthoesters as useful glycosyl donors in glycosylation reactions: A comparison with n-pent-4-enyl 1,2-orthoesters

Mannopyranose-derived methyl 1,2-orthoacetates (R = Me) and -benzoates (R = Ph) can function as glycosyl donors - upon BF3·Et 2O activation in CH2Cl2 - in glycosylation reactions with monosaccharide acceptors to afford disaccharides in good yields. In the process, glycosylation is preferred to acid-catalyzed rearrangement leading to methyl mannopyranosides. Methyl 1,2-orthoesters can be also used in regioselective glycosylation protocols with monosaccharide diols, in which they display good regioselectivity. Copyright

Variations on the SnCl4 and CF3CO2Ag-promoted glycosidation of sugar acetates: a direct, versatile and apparently simple method with either α or β stereocontrol

Glycosidation of sugar peracetates (d-gluco, d-galacto) with SnCl4 and CF3CO2Ag led to either 1,2-cis-, or 1,2-trans-glycosides, depending primarily on the alcohols used. In particular, 1,2-trans-glycosides, expected from acyl-protected glycosyl donors, were formed in high yields with alcohols sharing specific features such as bulkiness, presence of electron-withdrawing groups or polyethoxy motifs. In contrast, simple alcohols afforded ～1:1 mixtures of 2,3,4,6-tetra-O-acetyl, and 3,4,6-tri-O-acetyl 1,2-cis-glycosides due to anomerization and/or acid-catalyzed fragmentation of 1,2-orthoester intermediates. After reacetylation or deacetylation, acetylated or fully deprotected 1,2-cis-glycosides (α-d-gluco, α-d-galacto) were obtained in ～90% yields by a simple and direct method.

Novel methods for the preparation of partially acetylated carbohydrates

The selective acetylation of methyl α-D-hexopyranosides in the presence of zinc chloride shows unusual reactivity patterns compared to control experiments.Hydroperoxide ion is a mild and selective deacetylation reagent which does not attack primary acetates.