6586-70-5

Upstream product

• 23661-29-2 phenyl 2,3,4,6-tetra-O-acetyl-1-seleno-β-D-glucopyranoside 
• 67-63-0 isopropyl alcohol 
• 4860-85-9 methyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 333-27-7 methyl trifluoromethanesulfonate 

Downstream Products

• 5391-17-3 1-O-isopropyl-β-D-glucopyranoside 
• 55508-29-7 isopropyl β-D-thiogalactopyranoside 
• 114232-94-9 isopropyl 4,6-O-benzylidene-β-D-glucopyranoside 
• 59531-24-7 2,3,4,6-tetra-O-benzyl-D-glucopyranoside 
• 6564-72-3 2,3,4,6-tetra-O-benzyl-D-glucopyranose 
• 80300-30-7 1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-glucopyranose 
• 4451-36-9 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl chloride 
• 4451-35-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl chloride 
• 114967-51-0 isopropyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside 

Relevant academic research and scientific papers

Glycosyl alkoxythioimidates as building blocks for glycosylation: A reactivity study

Structural modifications of the leaving group of S-glycosyl O-methyl phenylcarbamothioates (SNea) involving change of substituents that express different electronic effects led to a better understanding of how the reactivity of these glycosyl donors can b

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.

THIOGLYCOSIDES AS POTENTIAL GLYCOSYL DONORS IN ELECTROCHEMICAL GLYCOSYLATION REACTIONS. PART 1: THEIR PREPARATION AND REACTIVITY TOWARD SIMPLE ALCOHOLS

Costant potential electrolysis of several glycosyl donors such as substituted phenyl 2,3,4,6-tetra-O-acetyl, benzoyl or benzyl-1-thio-β-D-gluco or galactopyranosides in dry acetonitrile in the presence of various primary, secondary or tertiary alcohols performed in an undivided cell, gave preferentially β-linked saccharides in moderate to good yields according to the nature of the protective groups on the sugar moiety. 2-Deoxy-2-phthalimido-1-thio-β-D-gluco derivatives gave the β-glucosides selectively in excellent yields.It was found, as expected, that substitution of the phenyl group with methoxy or methyl radicals facilitates the electrochemical glycosylation reaction by lowering the oxidation potentials of the corresponding thioglycosides.