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Synthesis of carbocyclic analogues of the mannosyl trisaccharide: ether- and imino-linked methyl 3,6-bis(5a-carba-α-d-mannopyranosyl)-3,6-dideoxy-α-d-mannopyranosides

✍ Scribed by Seiichiro Ogawa; Shin-ichi Sasaki; Hidetoshi Tsunoda

Publisher: Elsevier Science
Year: 1995
Tongue: English
Weight: 840 KB
Volume: 274
Category: Article
ISSN: 0008-6215
DOI: 10.1016/0008-6215(95)00121-9

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✦ Synopsis

Carbocyclic analogues 2 and 3 of the "trimannosyl structure 1", methyl 3,6-bis(5a-carba-a-Dmannopyranosyl)-3,6-dideoxy-a-D-mannopyranosides bonded by way of respective ether and imino linkages, were synthesized. The ether 2 had no inhibitory activity against a-D-mannosidase; in contrast, the imino compound 3 was a mild inhibitor. Furthermore, the inhibitory activity of 4, related to 3 by introduction of unsaturation between C-5 and C-5a of the carba-sugar moieties, was shown to be somewhat greater.

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