TY - JOUR
AU1 - Milne, George H.
AU2 - Townsend, Leroy B.
AB - 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.
TI - The synthesis and chemical reactivity of 6‐selenoguanosine and certain related derivatives
JF - Journal of Heterocyclic Chemistry
DO - 10.1002/jhet.5570080305
DA - 1971-06-01
UR - https://www.deepdyve.com/lp/wiley/the-synthesis-and-chemical-reactivity-of-6-selenoguanosine-and-certain-VuN4i6krnv
SP - 379
EP - 382
VL - 8
IS - 3
DP - DeepDyve
ER -