The use of the wittig reaction in the modification of purine nucleosides | Zendy

Montgomery John A. | Zendy; Laseter Anne G. | Zendy; Hewson Kathleen | Zendy

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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.

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