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Ramberg–Bäcklund Approaches to the Synthesis of C‐Linked Disaccharides
Author(s) -
Griffin Frank K.,
Paterson Duncan E.,
Taylor Richard J. K.
Publication year - 1999
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/(sici)1521-3773(19991004)38:19<2939::aid-anie2939>3.0.co;2-s
Subject(s) - computer science , computational biology , biology
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.