Deoxygenation of thiazolylketose acetates using SmI2-(CH2OH)2 or TMSOTf-Et3SiH affords thiazolyl C-glycosides with opposite α/β ratios. Examination of the thiazolyl α- and β-C-ribofuranoside pair by NOE experiments reveals that the earlier configuration assigned to one of these isomers has to be revised. Having prepared authentic anomeric α- and β-ribofuranose aldehydes from the corresponding thiazolyl C-glycosides by cleavage of the thiazole ring, each aldehyde was transformed into (1→6)-C-disaccharides via Wittig olefination with a galactose 6-phosphorane. © 2001 Elsevier Science Ltd. All rights reserved.

Selectivity in the SmI2-induced deoxygenation of thiazolylketoses for formyl C-glycoside synthesis and revised structure of C-ribofuranosides

DONDONI, Alessandro;FORMAGLIO, PAOLO;MARRA, Alberto;MASSI, Alessandro
2001

Abstract

Deoxygenation of thiazolylketose acetates using SmI2-(CH2OH)2 or TMSOTf-Et3SiH affords thiazolyl C-glycosides with opposite α/β ratios. Examination of the thiazolyl α- and β-C-ribofuranoside pair by NOE experiments reveals that the earlier configuration assigned to one of these isomers has to be revised. Having prepared authentic anomeric α- and β-ribofuranose aldehydes from the corresponding thiazolyl C-glycosides by cleavage of the thiazole ring, each aldehyde was transformed into (1→6)-C-disaccharides via Wittig olefination with a galactose 6-phosphorane. © 2001 Elsevier Science Ltd. All rights reserved.
2001
Dondoni, Alessandro; Formaglio, Paolo; Marra, Alberto; Massi, Alessandro
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11392/1201420
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