20771-15-7

Upstream product

• 108-24-7 acetic anhydride 
• 709-50-2 methyl beta-D-glucopyranoside 
• 67-56-1 methanol 
• 604-69-3 β-D-glucose pentaacetate 
• 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 

Downstream Products

• 146365-36-8 methyl 3,4,6-tri-O-acetyl-2-O-trityl-β-D-glucopyranoside 
• 139710-69-3 methyl-3,4,6-tri-O-acetyl-2-O-(3,4,6-tri-O-acetyl-2-O-benzyl-α-D-glucopyranosyl)-β-D-glucopyranoside 
• 908576-16-9 methyl-[O²-(toluene-4-sulfonyl)-β-D-glucopyranoside] 
• 769870-73-7 methyl-(O³-aza-β-D-altropyranoside) 
• 7226-39-3 2-deoxy-2-fluoro-D-mannopyranoside 
• 7226-42-8 1,3,4,6-tetra-O-acetyl-2-deoxy-2-fluoro-α-D-mannopyranoside 

Relevant academic research and scientific papers

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.

Reagent-dependent regioselective control in multiple carbohydrate esterifications

(Chemical Equation Presented) Regioselective control in organotin-mediated multiple acylation of carbohydrates is presented. The acylation reagent could be efficiently used to direct the product formation. Reagent-dependent thermodynamic and kinetic contr