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Synthesis of Some Analogues of Methyl Dehydro-oligobiosaminide (Acarviosin) by Seiichiro Ogawa; Kuninobu Yasuda; Tohei Takagaki; Yoshikazu Iwasawa; Tetsuo Suami is a scholarly article available to read on EtoBox.

What is Synthesis of Some Analogues of Methyl Dehydro-oligobiosaminide (Acarviosin) about?

The title pseudo-disaccharide, methyl 4,6-dideoxy-C{[(lS)-(1,4,6/5)-4,5,6trihydroxy-3-hydroxymethyl-2-cyclohexen-l-yl]amino}-D-glucopyranoside, is an essential core unit of several pseudo-oligosaccharidic a-D-glucosidase inhibitors2, which was initially obtained3 as the methyl a-glycoside (1) by acid-catalysed methanolysis of oligostatin C. The reaction was considered to involve dehydration of the axial hydroxyl group originally located on the cyclohexane ring. Alternatively, 1 (designated as acarviosin) was isolated in a pure form4, and was shown to be five times more potent an inhibitor than acarbose, whereas the p anomer exhibits only 5% activity". We have been interested in the structure-activity relationship for this kind of inhibitor and have described' the synthesis of a core unit of oligostatins by condensation of the amino sugar with a protected (hydroxymethyl)cyclohexanediol epoxide. We now report a synthesis of some protected derivatives of the stereoisomers (2-5) of 1. Condensation of methyl 4-amino-4,6-dideoxy-cw-D-glucopyranosides (6) with DL-3,4-di-O-acetyl-l,2-anhydro-(l,2,3/4)-5-benzoyloxymethyl-5-cyclohexene- ## CH,OH HO CCH,

Author

Seiichiro Ogawa; Kuninobu Yasuda; Tohei Takagaki; Yoshikazu Iwasawa; Tetsuo Suami

Publisher

Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0008-6215)

Published

1985

Language

EN