A Simple Access to Carbocyclic Analogs of 2-Deoxy-d-Ribose Having the 3-Hydroxymethylene Moiety Replaced by Heteroatoms
作者:
Karsten Schürrle,
Wolfgang Piepersberg,
期刊:
Journal of Carbohydrate Chemistry
(Taylor Available online 1996)
卷期:
Volume 15,
issue 4
页码: 435-447
ISSN:0732-8303
年代: 1996
DOI:10.1080/07328309608005664
出版商: Taylor & Francis Group
数据来源: Taylor
摘要:
(2S,4S)-1-O-Benzyl-2,5-di-O-mesyl-4-O-methoxymethylpentan-1,2,4,5-tetrol, a versatile precursor for subsequent cyclisations with bivalent nucleophiles, was obtained in five steps from the easily accessible (3S,5S)-3-hydroxy-5-hydroxymethyldihydrofuran-2(3H)-one. Using diso-dium phosphide in DMSO or disodium selenide in acetone-water, (2R,4S)-2-benzyloxymethyl-4-O-methoxymethylphospholane and (2R,4S)-2-benzyloxymethyl-4-O-methoxymethylselenolane were prepared. The phospholane was oxidized by oxygen (hydrogen peroxide) to give the analogous cyclic phospholane oxide (phosphinic acid) which was then transformed with benzyl bromide and alkali carbonate into the 1-benzyl phospholane oxide (phosphinic acid benzyl ester). All heterocyclic compounds sythesized, formally resemblecarba-2,3-dideoxy-d-giycero-pentofuranose, the carbocyclic analog of 2-deoxy-α-d-ribofuranose.
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