A NEW ROUTE TO THE SYNTHESIS OF CYCLITOL DERIVATIVES

Three cyclitol derivatives, 2, 4/3-triacetoxycyclohexanone diethyl dithioketal (XVIII), and 2, 3, 4-tri-O-acetyl-1-O-ethyl-2, 4/1, 3-cyclohexanetetrol (XXA) and 2, 3, 4-tri-O-acetyl-1-O-ethyl-1, 2, 4/3-cyclohexanetetrol (XXB), have been synthesized via the cyclisation of 2, 3, 4-tri-O-acetyl-5, 6-di...

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Bibliographic Details
Published in:Journal of antibiotics 1978, Vol.31(10), pp.1007-1012
Main Authors: OTHMAN, ADIL A., AL-MASUDI, NAJIM A., AL-TIMARI, USAMA S.
Format: Article
Language:English
Subjects:
Anti-Bacterial Agents - biosynthesis
Chemical Phenomena
Chemistry
Cyclization
Cyclohexanols - biosynthesis
Cyclohexanones - biosynthesis
Molecular Conformation
Photolysis
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Summary:Three cyclitol derivatives, 2, 4/3-triacetoxycyclohexanone diethyl dithioketal (XVIII), and 2, 3, 4-tri-O-acetyl-1-O-ethyl-2, 4/1, 3-cyclohexanetetrol (XXA) and 2, 3, 4-tri-O-acetyl-1-O-ethyl-1, 2, 4/3-cyclohexanetetrol (XXB), have been synthesized via the cyclisation of 2, 3, 4-tri-O-acetyl-5, 6-dideoxy-D-xylo-hex-5-enose diethyl dithioacetal (XIV) and the cyclisation of 2, 3, 4-tri-O-acetyl-5, 6-dideoxy-D-xylo-hex-5-enose diethyl acetal (XV) under ultraviolet or direct sunlight, in aqueous acetone.
ISSN:0021-8820
1881-1469
DOI:10.7164/antibiotics.31.1007