Ramberg-Bäcklund Approaches to the Synthesis of C-Linked Disaccharides

Readily available S‐glycoside dioxides were utilized in a Ramberg–Bäcklund rearrangement for the construction of C‐linked disaccharides. This approach is ideally suited to analogue synthesis simply by variation of the alkylating agent, and is illustrated here by the synthesis of β,β‐C‐trehalose (see...

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Published inAngewandte Chemie International Edition Vol. 38; no. 19; pp. 2939 - 2942
Main Authors Griffin, Frank K., Paterson, Duncan E., Taylor, Richard J. K.
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag GmbH 04.10.1999
WILEY‐VCH Verlag GmbH
Wiley
Subjects
Chemistry
Chemistry, Multidisciplinary
Disaccharides
Glycosides
Physical Sciences
Rearrangements
Science & Technology
disaccharides
PREFERRED CONFORMATION
glycosides
EXO-GLYCALS
rearrangements
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Summary:Readily available S‐glycoside dioxides were utilized in a Ramberg–Bäcklund rearrangement for the construction of C‐linked disaccharides. This approach is ideally suited to analogue synthesis simply by variation of the alkylating agent, and is illustrated here by the synthesis of β,β‐C‐trehalose (see reaction scheme), a higher homologue of C‐trehalose, and methyl C‐gentiobioside. Bn=benzyl.
Bibliography:istex:30F7C874B8A96F13782A5246DE027664F285126B
ArticleID:ANIE2939
ark:/67375/WNG-N7PKWFPQ-C
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1433-7851
1521-3773
DOI:10.1002/(SICI)1521-3773(19991004)38:19<2939::AID-ANIE2939>3.0.CO;2-S