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Synthesis of some derivatives of pseudo-α-galactopyranose [(1,2/3,4,5)-5-hydroxymethyl-1,2,3,4-cyclohexanetetrol]

✍ Scribed by Seiichiro Ogawa; Yasushi Shibata; Keiko Miyazawa; Tatsuhi Toyokuni; Tatsuo Iida; Tetsuo Suami

Publisher
Elsevier Science
Year
1987
Tongue
English
Weight
655 KB
Volume
163
Category
Article
ISSN
0008-6215

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✦ Synopsis

Isopropylidenation of ~~-(1,2/3,4,5)-5-hydroxymethyl-l,2,3,4-cyclohexanetetrol (1) with 2,2-dimethoxypropane in N,N-dimethylformamide in the presence of toluene-p-sulfonic acid gave the 1,2:3,4-, 1,2:4,7-, and 2,3:4,7-di-O-isopropylidene derivatives. Several C-7 substituted derivatives of 1 of biological interest have been prepared by nucleophilic displacement reactions of the tosylate derived from the most readily available 1,2:3,4-di-0isopropylidene derivative 3. Condensation of 3 with 2,3,4,6-tetra-0-acetyl-ar-o-glucopyranosyl bromide gave diastereoisomeric products, which were converted into 7-O-@D-glucopyranosyl)-pseudo-a-D-(%A) and +galactopyranose (XB), the structures of which were confirmed by degradation of the octa-acetate of %A, yielding the known pseudo-c+D-galactopyranose penta-acetate. *Pseudo-sugars, Part XVII. For Part XVI, see ref. 1. **To whom correspondence should be addressed.

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