Journal of Carbohydrate Chemistry

Serine and Threonine Schiff Base Esters React with β-Anomeric Peracetates in the Presence of BF3· Et2O to Produce β-Glycosides

CM Keyari, R Polt

文献索引：Keyari, Charles M.; Polt, Robin Journal of Carbohydrate Chemistry, 2010 , vol. 29, # 4 p. 181 - 206

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被引用次数: 14

摘要

Improved procedures are reported for the glycosylation of L-serine and L-threonine utilizing activated Schiff base glycosyl acceptors, which are less expensive and more efficient alternatives to published methods. L-serine or L-threonine benzyl ester hydrochloride salts were reacted with the diarylketimine bis-(4-methoxyphenyl)-methanimine in CH3CN at rt to form the more nucleophilic Schiff bases 3a and 3b in excellent yield. These Schiff bases ...