Neighboring-group participation in benzylidene acetal ring-opening of a 2-cyano-2-deoxypyranoside derivative by diethylaluminurn cyanide

The oxirane ring-opening of an anhydro sugar with diethylaluminum cyanide (Et2AlCN) is a direct approach for obtaining a cyano derivative. Methyl 2,3-anhydro-4,6-O-benzylidene-alpha-D-allopyranoside showed anomalous chemical behavior when treated with Et2AlCN. The reaction afforded the corresponding...

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Bibliographic Details
Published inCarbohydrate research Vol. 338; no. 21; pp. 2177 - 2183
Main Authors Mangione, MI, Suarez, AG, Spanevello, RA
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 10.10.2003
Subjects
Biochemistry & Molecular Biology
Chemistry
Chemistry, Applied
Chemistry, Organic
Life Sciences & Biomedicine
Physical Sciences
Science & Technology
NUCLEOSIDE
BRANCHED-CHAIN
benzylidene acetal
diethylaluminum cyanide
SUGARS
CLEAVAGE
2-cyano-2-deoxypyranoside
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Summary:The oxirane ring-opening of an anhydro sugar with diethylaluminum cyanide (Et2AlCN) is a direct approach for obtaining a cyano derivative. Methyl 2,3-anhydro-4,6-O-benzylidene-alpha-D-allopyranoside showed anomalous chemical behavior when treated with Et2AlCN. The reaction afforded the corresponding beta-cyanohydrin as the minor component from a mixture of compounds resulting from the benzylidene acetal ring-opening caused by the attack of ethyl or cyano groups. (C) 2003 Elsevier Ltd. All rights reserved.
ISSN:0008-6215
1873-426X
DOI:10.1016/S0008-6215(03)00377-X