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The use of the wittig reaction in the modification of purine nucleosides
Author(s) -
Montgomery John A.,
Laseter Anne G.,
Hewson Kathleen
Publication year - 1974
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570110219
Subject(s) - chemistry , wittig reaction , purine , diimide , ribonucleoside , stereochemistry , purine analogue , organic chemistry , molecule , biochemistry , enzyme , rna , perylene , gene
The Pfitzner‐Moffatt oxidation of 6‐chloro‐9‐(2,3‐ O ‐isopropylidene‐β‐D‐ribofuranosyl)purine, 9‐(2,3‐ O ‐isopropylidene‐β‐D‐ribofuranosyl)‐6‐(methylthio)purine, and 2′,3′‐ O ‐isopropylideneadenosine gave the corresponding 5′‐aldehydes (3, 13, and 4), which were allowed to react with a number of Wittig ylids. The resulting olefins, primarily trans , were reduced either catalytically or with diimide before removal of the 2′,3′‐ O ‐isopropylidene groups to give the desired 5′‐substituted purine ribonucleosides.