114192-64-2

Upstream product

• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 5927-18-4 trimethyl phosphonoacetate 
• 4132-28-9 2,3,4,6-tetra-O-benzyl-D-mannopyranose 
• 114192-63-1 1-Naphthalen-2-yl-2-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethanone 
• 56822-49-2 1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-glucopyranoside 
• 77086-38-5 ketene t-butyldimethylsilyl methyl acetal 
• 67-56-1 methanol 

Downstream Products

• 81972-20-5 2-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)ethanol 
• 124813-78-1 methyl 2-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)acetate 
• 124813-80-5 methyl 2-(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl)acetate 
• 124813-79-2 methyl 2-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)acetate 

Relevant academic research and scientific papers

The Wittig-Horner Reaction on 2,3,4,6-Tetra-O-benzyl-D-mannopyranose and 2,3,4,6-Tetra-O-benzyl-D-glucopyranose

The synthetic utility of the Wittig-Horner reaction in the synthesis of C-glycosides is illustrated by the preparation of the α- and β-glycosyl acetates of the 2,3,4,6-tetra-O-benzyl-D-mannopyranose and of the 2,3,4,6-tetra-O-benzylglucopyranose.A partial epimerization of the C-2 carbon of the starting protected carbohydrate is observed.

β-selective C-glycosidations: Lewis-acid mediated reactions of carbohydrates with silyl ketene acetals

Several examples of β-selective C-glycosidation reactions, involving TMSOTf-promoted addition of sterically hindered silyl ketene acetals to glucosyl and galactosyl acetates, are presented.

The First Direct Method for C-Glucopyranosyl Derivatization of 2,3,4,6-Tetra-O-benzyl-D-glucopyranose

Commercially available 2,3,4,6-tetra-O-benzyl-D-glucopyranose, activated by trifluoroacetic anhydride reacts, in the presence of Lewis acids, with various silyl enol ethers or with allylsilane to yield C-D-glucopyranosyl derivatives of the α-configuration