Nickel(II)-Catalysed Transformations of 5-Azido-5-deoxy-d-glucofuranose and of 5-Azido-5-deoxy-l-idofuranose
作者:
Philipp Hadwiger,
Andreas Lechner,
ArnoldE. Stütz,
期刊:
Journal of Carbohydrate Chemistry
(Taylor Available online 1998)
卷期:
Volume 17,
issue 2
页码: 241-247
ISSN:0732-8303
年代: 1998
DOI:10.1080/07328309808002325
出版商: Taylor & Francis Group
数据来源: Taylor
摘要:
Nickel(II) catalysed isomerisation reactions of C-5 modified derivatives of D-glucose as well as L-idose were investigated. 5-Azido-5-deoxy-D-glucofuranose was successfully isomerised into the corresponding D-mannoepimer in good yields. Contrasting this result, in the case of the 5-modified L-idofuranose probed, no evidence for successful epimerisation at C-2 could be found. However, this sugar was quantitatively rearranged into the corresponding L-sorbopyranose. Upon extended reaction periods, the latter underwent degradation to give the coresponding 4-modified methyl L-xylonate.
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