4.4 Article

A fused GaINAc-thiazole from a singular and unanticipated fragmentation

Journal

TETRAHEDRON LETTERS
Volume 45, Issue 46, Pages 8507-8510

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2004.09.091

Keywords

retro-aldol; rearrangement; aromatization

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Attempted O-desilylation of an elaborated GalNAc-thiazoline t-butyl ester gave rise instead to a GalNAc-thiazole wherein the two-carbon acetate side chain has been severed by a process heretofore undescribed. The corresponding ether ester rearranged to a C-furanoside by a quite different pathway. (C) 2004 Elsevier Ltd. All rights reserved.

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