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Synthesis 2009(16): 2756-2760
DOI: 10.1055/s-0029-1217605
DOI: 10.1055/s-0029-1217605
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Stereocontrolled Formation of Protected Aminodeoxyalditols from Simple Carbohydrate Precursors by Debenzylating Cycloetherification
Further Information
Received
3 March 2009
Publication Date:
10 July 2009 (online)
Publication History
Publication Date:
10 July 2009 (online)
Abstract
A new and highly efficient methodology for the stereocontrolled synthesis of aminodeoxyalditols is described through a dimesylation/intramolecular SN2 nucleophilic substitution ring-forming reaction sequence from glucose, mannose, and galactose derivatives. The degree of difficulty and rate of the reaction of dimesylates in the cyclization process is evaluated and shows the trend: galactose > glucose > mannose derivatives, which has been identified from our experiments and classical theories.
Key words
intramolecular cyclization - debenzylation - anhydrosugar - azido group - stereocontrolled synthesis
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