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Unexpected Formation of 3,6-Anhydrofuranoses by Acid Treatment of Methyl 2,3-Di-O-acyl-D-glycopyranosides

✍ Scribed by Ziegler, Thomas ;Vollmer, Martin ;Oberhoffner, Sven ;Eckhardt, Elisabeth

Book ID
102901907
Publisher
John Wiley and Sons
Year
1993
Tongue
English
Weight
596 KB
Volume
1993
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

Treatment of methyl 2,3‐di‐O‐acyl‐D‐glycopyranosides 1 of glucose and mannose with catalytic amounts of trifluoromethanesulfonic acid afforded the corresponding bis(5‐O‐acyl‐3,6‐anhydro‐D‐glycofuranose) 1,2′:2,1′‐dianhydrides 6 in 12–58% yield the structure of which was confirmed for the α‐D‐glucose derivative 6a by an X‐ray analysis. In addition, in the presence of methyl pyruvate (2a) or methyl 2‐acetoxy‐acrylate (2b) various amounts of diastereomeric 3,6‐anhydro‐5‐O‐benzoyl‐1,2‐O‐(1‐methoxycarbonyl)ethylidene‐α‐D‐glucofuranoses 5 and acylated methyl α‐D‐glucopyranosides 3 and 4, respectively, were formed.

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