The effect of replacing a 3-O-acetyl group by a 3-O-benzyl group in a methyl 4-O-trityl-β-d-xylopyranoside derivative on the efficiency of 1,2-trans-glycosylation with a d-xylose 1,2-O-(1-cyanoethylidene) derivative

Add time:08/30/2019    Source:sciencedirect.com

Replacement of AcO-3 in methyl 2,3-di-O-acetyl-4-O-trityl-β-d-xylopyranoside with a benzyl group greatly increases the 1,2-trans-stereoselectivity of glycosylation with a d-xylopyranose 1,2-O-(1-cyanoethylidene) derivative. Anomerisation of methyl 2-O-benzyl-β-d-xylopyranoside derivatives occurred under the action of triphenylmethylium perchlorate.

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