A Simple Access to Carbocyclic Analogs of 2-Deoxy-d-Ribose Having the 3-Hydroxymethylene Moiety Replaced by Heteroatoms
Title:
A Simple Access to Carbocyclic Analogs of 2-Deoxy-d-Ribose Having the 3-Hydroxymethylene Moiety Replaced by Heteroatoms
Author:
Schurrle, Karsten Piepersberg, Wolfgang
Appeared in:
Journal of carbohydrate chemistry
Paging:
Volume 15 (1996) nr. 4 pages 435-447
Year:
1996-05-01
Contents:
(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 resemble carba-2,3-dideoxy-d-giycero-pentofuranose, the carbocyclic analog of 2-deoxy-α-d-ribofuranose.
Journal description