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Syntheses of β-C(1→3)-Glucopyranosides of 2- and 4-Deoxy-D-hexoses

✍ Scribed by Raynald Demange; Carine Bühlmann; Pierre Vogel

Publisher
John Wiley and Sons
Year
2003
Tongue
German
Weight
260 KB
Volume
86
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

The OshimaNozaki (Et~2~AlI) condensation of isolevoglucosenone (4) with 2,6‐anhydro‐3,4,5,7‐tetra‐O‐benzyl‐D‐__glycero‐D‐gulo‐heptose (5) gave an enone 6 that was converted with high stereoselectivity to 3‐C‐[(1__R)‐2,6‐anhydro‐D‐__glycero‐D‐gulo‐heptitol‐1‐C‐yl]‐2,3‐dideoxy‐D‐arabino‐hexose (1; 1 : 1 mixture of α‐ and β‐D‐pyranose), and to 3‐C‐[(1__R)‐2,6‐anhydro‐D‐__glycero‐D‐gulo‐heptitol‐1‐C‐yl]‐2,3‐dideoxy‐D‐lyxo‐hexose (2; 2.7 : 1.4 : 1.0 : 1.4 mixture of α‐D‐furanose, β‐D‐furanose, α‐D‐pyranose, and β‐D‐pyranose). The OshimaNozaki (Et~2~AlI) condensation of levoglucosenone (17) with aldehyde 5 gave an enone 18 that was converted with high stereoselectivity to 3‐C‐[(1__R)‐2,6‐anhydro‐D‐__glycero‐__D‐gulo‐heptitol‐1‐C‐yl]‐3,4‐dideoxy‐α‐D‐arabino‐hexopyranose (3; single anomer).

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