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Synthesis 2006(4): 699-705
DOI: 10.1055/s-2006-926297
DOI: 10.1055/s-2006-926297
PAPER
© Georg Thieme Verlag Stuttgart · New York
Preparation of Ethyl 2-Azido-2-deoxy-1-thio-β-d-mannopyranosides, and their Rearrangement to 2-S-Ethyl-2-thio-β-d-mannopyranosylamines
Further Information
Received
2 May 2005
Publication Date:
11 January 2006 (online)
Publication History
Publication Date:
11 January 2006 (online)
Abstract
The synthesis of ethyl 2-azido-2-deoxy-1-thio-β-d-mannopyranosides 7-11, starting from appropriate synthons with gluco configuration, via SN2 substitution at C(2), and their rearrangement to 2-S-ethyl-2-thio-β-d-mannopyranosylamines 12-14 are presented.
Key words
carbohydrates - d-mannosamine - thioglycosides - stereoselective synthesis - intramolecular rearrangements
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