88559-80-2

Upstream product

• 57783-66-1 benzyl 4,6-O-benzylidene-2,3-tri-O-benzyl-β-D-glucopyranoside 
• 67831-42-9 benzyl 2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 183960-31-8 Acetic acid (2S,3R,4S,5R,6R)-3-acetoxy-6-acetoxymethyl-5-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-2-((2R,3R,4S,5R,6R)-4,5,6-tris-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-4-yl ester 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 

Downstream Products

• 88567-44-6 benzyl O-(4,6-O-benzylidine-β-D-glucopyranosyl)-(1->4)-O-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 

Relevant academic research and scientific papers

β-acarbose. II. The preparation of various carbohydrate trifluoromethanesulfonates

Three carbohydrate trifluoromethanesulfonates, of potential use in the alkylation of a 1-epivalienamine derivative to produce precursors of β-acarbose, have been prepared from the appropriate alcohols. The conversion of two of these trifluoromethanesulfonates into the primary amine, via the corresponding azide, is also reported.

SYNTHESIS OF CELLOBIOSE, CELLOTRIOSE, CELLOTETRAOSE, AND LACTOSE

Condensation of 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (1) with benzyl 2,3,6-tri-O-benzyl-β-D-glucopyranoside (6) in 1:1 benzene-nitromethane in the presence of mercuric cyanide gave, in 86percent yield after O-deacetylation followed by column chromatography, benzyl 2,3,6-tri-O-benzyl-β-cellobioside, which was catalytically hydrogenolyzed to afford cellobiose.In a similar way, methyl-α-cellobioside cellotriose, methyl-α- and β-cellotriosides, cellotetraose, lactose, and methyl α-lactoside were synthesized with high stereospecificity and in good yield by the coupling reaction, using methyl 2,3,6-tri-O-benzyl-α- and -β-D-glucopyranosyde, 6, and benzyl 2,3,6,2',3',6'-hexa-O-benzyl-β-cellobioside as the glycosyl acceptors, and 1, 2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl bromide, and hepta-O-acetyl-α-cellobiosyl bromide as the glycosyl donors.