Alicyclic Carbohydrates. XXIX.1,2 The Synthesis of a Pseudo-Hexose (2,3,4,5-Tetrahydroxycyclohexanemethanol)
Alicyclic Carbohydrates. XXIX.1,2 The Synthesis of a Pseudo-Hexose (2,3,4,5-Tetrahydroxycyclohexanemethanol)
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脂环族碳水化合物。
DOI：
10.1021/jo01343a048
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发表时间：
1966
影响因子：
3.6
通讯作者：
L. Durham
中科院分区：
文献类型：
--
作者：
G. Mccasland;S. Furuta;L. Durham
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The expression “pseudo-sugar” is proposed to designate any alicyclic analog of a cyclic monosaccharide, in which the usual ring-oxygen atom is replaced by methylene. A compound, 2, 3, 4, 5-tetrahydroxycyclohexanemethanol, has been synthesized and appears to be the first known pseudo-hexose. It has the ct-niAalopyranose configuration. It was obtained by reduction of the corresponding tetraacetoxycyclohexanecarboxylic acid methyl ester which had been preparedby a Diels-Alder synthesis from 2-acetoxyfuran and maleic anhydride. Pentaacetate and trityl ether tetraacetate derivatives were also prepared. With the aid of nmr spectroscopy, it was established that the conformation with side chain equatorial was preferred for the pseudo-hexose and its derivatives. Conformational assignments were based upon spin-spin coupling patterns and comparisons with other spectra in the same series.