Synthesis of Spacer-Linked Tail to Tail Dimers Derived from a Conformationally Rigid Aminodeoxysugar by Olefin Metathesis

Andreas Kirschning; Guang-Wu Chen

doi:10.1055/s-2000-6328

Synthesis 2000; 2000(8): 1133-1137
DOI: 10.1055/s-2000-6328

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Synthesis of Spacer-Linked Tail to Tail Dimers Derived from a Conformationally Rigid Aminodeoxysugar by Olefin Metathesis

Andreas Kirschning^* , Guang-Wu Chen

^*Institut für Organische Chemie der Technischen Universität Clausthal, Leibnizstraße 6, D-38678 Clausthal-Zellerfeld, Germany; Fax (+) (0) 53 23 72 28 58; E-mail: andreas.kirschning@tu-clausthal.de

Abstract

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The preparation of new tail to tail dimers of bridged aminodeoxysugars 2 and 11 is described. The first key step in the synthesis is the formation of the aminomethyl bridge in the carbohydrate-derived monomer 7 which is achieved by silver promoted ring closure of methyl 3-acetamido-6-bromo-2,3,6-trideoxy α-d-glucoside 6. Secondly, olefin metathesis of the corresponding 4-O-allyl glycoside 9 constitutes a powerful tool for dimerization, which allows synthesis of 1,4-butanediol-linked tail to tail neooligosaccharides 2 and 11.

neooligosaccharide - metathesis - aminodeoxysugar - conformational restriction

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