Strategies for stereocontrol at C1 or C2 in syntheses of α-glucosaminides

The C1 and C2 stereocenters of α‐glucosaminides can be prepared by establishing the stereocenters in either order. For the former, a C2‐azido glucosyl donor is prepared first, and the restraining effect of a 4,6‐O‐benzylidene ring is used to induce α‐coupling. For the latter, the C1 linkage is prepa...

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Bibliographic Details
Published in:Israel journal of chemistry 2000-12, Vol.40 (3-4), p.255-262
Main Authors: Fraser-Reid, Bert, Anilkumar, G., Nair, Latha G., Olsson, Lars, Martin, Mercedes Garcia, Daniels, Jacquitta K.
Format: Article
Language:English
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Summary:The C1 and C2 stereocenters of α‐glucosaminides can be prepared by establishing the stereocenters in either order. For the former, a C2‐azido glucosyl donor is prepared first, and the restraining effect of a 4,6‐O‐benzylidene ring is used to induce α‐coupling. For the latter, the C1 linkage is prepared first by use of an n‐pentenyl‐manno‐1,2‐orthoester donor which ensures (a) clean α‐coupling and (b) a convenient C2‐ester. The C2‐ester is replaced with a triflate leaving group, and nucleophilic displacement is effected by use of a hypervalent silicon azide.
ISSN:0021-2148
1869-5868
DOI:10.1560/KDP7-D0BA-BN04-3H3A