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Synthesis of pseudo-trehaloses: [(1,2,43,5)-2,3,4-trihydroxy-5-hydroxymethyl-1-cyclohexyl] d-glucopyranosides

✍ Scribed by Seiichiro Ogawa; Shigeki Yokoi; Noritaka Kimura; Yasushi Shibata; Noritaka Chida

Publisher: Elsevier Science
Year: 1988
Tongue: English
Weight: 634 KB
Volume: 181
Category: Article
ISSN: 0008-6215
DOI: 10.1016/0008-6215(88)84022-9

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✦ Synopsis

All the theoretically possible, four diastereoisomeric pairs, qcy (2A and 2B), cr,p (3A and 3B), P,(Y (4A and 4B), and &/3 (5A and 5B), of pseudo-trehalose, composed of D-glucopyranose and pseudo-D-or L-glucopyranose, have been synthesiscd by coupling of the appropriately protected pseudo-a-(6) and -P-DL-@COpyranoses (9) with D-glucopyranose derivatives (10 and 11) in the presence of trimethylsilyl trifluoromethanesulfonate. Elucidation of the structures and absolute configurations of the pseudo-disaccharides was based on the 'H-n.m.r. spectra of their octa-acetates and the optical rotations. None of the pseudo-trehaloses inhibited trehalase.

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