151807-96-4

Upstream product

• 6988-40-5 methyl 2,3-di-O-benzyl-β-D-glucopyranoside 
• 101312-02-1 methyl 2,3-di-O-benzyl-4,6-di-O-benzylidene-β-D-glucopyranoside 

Downstream Products

• 151807-97-5 methyl 2,3-di-O-benzyl-6-O-deoxy-β-D-xylo-hex-5-enopyranoside 
• 176380-03-3 methyl 2,3‐di‐O‐benzyl‐6‐deoxy‐β‐D‐glucopyranoside 
• 51433-17-1 Methyl 2,3-di-O-benzyl-4-O-methyl-β-D-glucopyranoside 
• 6988-42-7 methyl 2,3-di-O-benzyl-6-deoxy-β-D-galactopyranoside 
• 190379-06-7 Trifluoro-methanesulfonic acid (2R,3S,4R,5R,6R)-4,5-bis-benzyloxy-6-methoxy-2-methyl-tetrahydro-pyran-3-yl ester 
• 43086-96-0 methyl 4-azido-2,3-di-O-benzyl-4,6-dideoxy-β-D-glucoside 
• 785806-47-5 (2R,4R,5R,6R)-4,5-Bis-benzyloxy-6-methoxy-2-methyl-dihydro-pyran-3-one 

Relevant academic research and scientific papers

Mapping the Relationship between Glycosyl Acceptor Reactivity and Glycosylation Stereoselectivity

The reactivity of both coupling partners—the glycosyl donor and acceptor—is decisive for the outcome of a glycosylation reaction, in terms of both yield and stereoselectivity. Where the reactivity of glycosyl donors is well understood and can be controlled through manipulation of the functional/protecting-group pattern, the reactivity of glycosyl acceptor alcohols is poorly understood. We here present an operationally simple system to gauge glycosyl acceptor reactivity, which employs two conformationally locked donors with stereoselectivity that critically depends on the reactivity of the nucleophile. A wide array of acceptors was screened and their structure–reactivity/stereoselectivity relationships established. By systematically varying the protecting groups, the reactivity of glycosyl acceptors can be adjusted to attain stereoselective cis-glucosylations.

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.

Silylmethylene radical cyclization. A stereoselective approach to branched sugars

Ethyl 6-O-benzyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside (2) was converted, in three steps and in 73percent overall yield, into ethyl 6-O-benzyl-2,3-dideoxy-3-C-(hydroxymethyl)-α-D-ribo-hex-2-enopyranoside.This transformation involved silylation of 2