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DETRITYLATION-ACYLATION AS A SIDE REACTION UPON GLYCOSYLATION OF TRITYL ETHERS WITH SUGAR 1 ,2 -O-(1-CYANO)ETHYLIDENE DERIVATIVES. EFFECT OF SOLVENT
TSVETKOV Yu. E., KITOV P. I., BACKINOWSKY L. V., KOCHETKOV N. K.
N. D. Zelinsky Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow
Abstract: 6-O-Acyl derivatives of 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose are formed as toy-products upon TrClO4-catalysed glycosylation of 1,2:3,4-di-O-isopropylidene-6-0-trityl-α-D-galactopyranose with 3,4,6-tri-O-acetyl-1,2-E-(1-cyanoalkylidene)-α-D-galactopyranoses. Increase in the solvent polarity hinders the formation of the by-products. The above side reaction is rationalised in terms of 1,2-orthoester intermediacy.
Russian Journal of Bioorganic Chemistry 1990, 16 (1):98-104