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Synthesis of four new diastereoisomers of dl-5-hydroxymethyl-1,2,3,4-cyclohexanetetrol

โœ Scribed by Seiichiro Ogawa; Yoshiki Tsukiboshi; Yoshikazu Iwasawa; Tetsuo Suami

Publisher
Elsevier Science
Year
1985
Tongue
English
Weight
1002 KB
Volume
136
Category
Article
ISSN
0008-6215

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โœฆ Synopsis

Four new diastereoisomers of the pseudo-sugar DL-5-hydroxymethyl-1,2,3,4cyclohexanetetrol, having (1,2,3,4/5)-(2), (1,5/2,3,4)-(3), (1,2,3/4,5)-(4), and (1,2,4,5/3)-configurations (5), have been synthesised by unambiguous sequences from readily available pseudo-sugars. Acetonation of DL-(1,2,4/3,5)-5-hydroxymethyl-1,2,3,4-cyclohexanetetrol with 2,2_dimethoxypropane in N,N-dimethylformamide in the presence of toluene-p-sulfonic acid gave the 1,2:4,7-di-Oisopropylidene derivative (9) in good yield. Oxidation of HO-3 in 9 with ruthenium tetraoxide in chloroform gave the ketone 11, which was catalytically hydrogenated to give the 3-epimer (12) of 9. Deprotection of 12 gave the 1,2,3,4/5isomer 2 in good yield. Likewise, compounds 3 and 4 were synthesised from (1,3,5/2,4)-and (1,2/3,4,5)-5-hydroxymethyl-l,2,3,4-cyclohexanetetrol, respectively. Compound 5 was obtained by catalytic hydrogenation of DL-(1 ,2,4/3)-5-hydroxymethyl-5cyclohexene-1,2,3,4_tetrol.

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