Journal
TETRAHEDRON-ASYMMETRY
Volume 13, Issue 16, Pages 1707-1711Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0957-4166(02)00473-1
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The synthesis of fused furanosyl beta-amino esters from protected sugar lactones is described, using the combination of a Wittig type reaction and 1,4-addition of benzylamine on the resulting glycosylidenes. This sequence of reactions afford either N-glycosyl-3-ulosonic acid esters, which are the beta-analogues of anomeric sugar alpha-amino esters, or open-chain sugar beta-enamino esters, when a retro-Michael reaction takes place after addition of benzylamine. Incorporation of the fused furanosyl beta-amino ester 2a into a peptide chain is also described. (C) 2002 Elsevier Science Ltd. All rights reserved.
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