One-Pot Synthesis of Tri-Acetalated Aldohexoses with 1,1-Dialkoxycyclohexane–p-Toluenesulfonic Acid
作者:
Makoto Kiso,
Akiyo Yasui,
Akira Hasegawa,
期刊:
Journal of Carbohydrate Chemistry
(Taylor Available online 1983)
卷期:
Volume 2,
issue 4
页码: 449-456
ISSN:0732-8303
年代: 1983
DOI:10.1080/07328308308057891
出版商: Taylor & Francis Group
数据来源: Taylor
摘要:
2-Deoxy-d-arabino-hexose (1), 2-acetamido-2-deoxy-d-glucose (2), and 2-deoxy-2-trifluoroacetamido-d-glucose (3) were each treated with 1,1-dimethoxycyclohexane or 1,1-dibenzyloxycyclohexane in 1,4-dioxane in the presence ofp-toluenesulfonic acid. The major products were the 1,1-dimethyl or 1,1-dibenzyl acetals (4-9) of 3,4:5,6-di-O-cyclohexylidene-2-deoxy-aldehydo-d-arabino-hexose, and of 2- (acylamino)-3,4:5,6-di-O-cyclohexylidene-2-deoxy-aldehydo-D-glucose. The dibenzyl acetal derivatives were converted, by hydro-genolysis, into the corresponding, acyclic aldehydes (10-12) in good yields.
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