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The synthesis and chemical reactivity of 6‐selenoguanosine and certain related derivatives
Author(s) -
Milne George H.,
Townsend Leroy B.
Publication year - 1971
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.5570080305
Subject(s) - chemistry , sodium methoxide , nucleophile , alkylation , raney nickel , purine , medicinal chemistry , selenide , group (periodic table) , stereochemistry , reactivity (psychology) , organic chemistry , selenium , hydrogen , methanol , catalysis , enzyme , medicine , alternative medicine , pathology
The synthesis of 6‐selenoguanosine ( 2 ) has been accomplished by a nucleophilic displacement of the chloro group from 2‐amino‐6‐chloro‐9‐(β‐ D ‐ribofuranosyl)purine ( 1 ) with either selenourea or sodium hydrogen selenide. Treatment of 2 with Raney nickel has revealed that the seleno group can be removed much easier under these conditions than the corresponding mercapto group. Alkylation of 2 with several alkylating agents occurred at the exocyclic 6‐seleno group to furnish several 6‐alkylseleno‐2‐amino‐9‐(β‐ D ‐ribofuranosyl)purines. Nucleophilic displacement of the 6‐benzylseleno group from 2‐amino‐6‐benzylseleno‐9‐(β‐ D ‐ribofuranosyl)purine ( 3c ) with sodium methoxide has been observed to occur at a faster rate than that observed for the corresponding 6‐benzylmercapto derivative. A study on the relative stability between 2 and 6‐seleno‐9‐(β‐ D ‐ribofuranosyl)purine toward basic conditions has revealed that the amino group at position two imparts an increase in stability.