Facile Synthesis of O 6-Alkyl-, O 6-Aryl-, and Diaminopurine Nucleosides from 2‘-Deoxyguanosine

The 3‘,5‘-bis-O-TBDMS derivative of 2‘-deoxyguanosine can be converted to its O 6-alkyl and O 6-aryl ethers as well as to N 6-substituted diaminopurine nucleosides in two simple steps. Also described is a novel, nonaqueous, one-step O 6-desulfonylation method that leads to deprotection of the carbon...

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Bibliographic Details
Published in:Organic letters 2000-04, Vol.2 (7), p.927-930
Main Authors: Lakshman, Mahesh K, Ngassa, Felix N, Keeler, John C, Dinh, Yen Q. V, Hilmer, John H, Russon, Larry M
Format: Article
Language:English
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Summary:The 3‘,5‘-bis-O-TBDMS derivative of 2‘-deoxyguanosine can be converted to its O 6-alkyl and O 6-aryl ethers as well as to N 6-substituted diaminopurine nucleosides in two simple steps. Also described is a novel, nonaqueous, one-step O 6-desulfonylation method that leads to deprotection of the carbonyl moiety of 2‘-deoxyguanosine.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol005564m