The Journal of Organic Chemistry

Glycosidase inhibitors: Synthesis of enantiomerically pure aza-sugars from Schiff base amino esters via tandem reduction-alkenylation and osmylation

R Polt, D Sames, J Chruma

Index: Polt, Robin; Sames, Dalibor; Chruma, Jason Journal of Organic Chemistry, 1999 , vol. 64, # 17 p. 6147 - 6158

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Citation Number: 37

Abstract

Nitrogen-in-the-ring “aza-sugars” have been synthesized in enantiomerically pure form from the amino acid l-alanine in excellent overall yield. The O'Donnell's Schiff base of l-alanine methyl ester 9a was converted to aza-sugar l-fuco-1-deoxy-nojirimycin, 18, and to the epimer l-gulo-1-deoxy-nojirimycin, 20, in eight steps. The overall yields were 20 and 29%, respectively. The methodology for the efficient generation of silyl-and benzyl-protected (E) ...