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Photochemical removal of the tosyl group from the 5′N position of 5′‐aminopyrimidine nucleosides: syntheticapplications
Author(s) -
Urjasz Wojciech,
Celewicz Lech
Publication year - 1998
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/(sici)1099-1395(199808/09)11:8/9<618::aid-poc52>3.0.co;2-f
Subject(s) - chemistry , tosyl , acetonitrile , amine gas treating , aqueous solution , thymidine , medicinal chemistry , organic chemistry , photochemistry , combinatorial chemistry , in vitro , biochemistry
The p ‐toluenesulfonyl (tosyl) group, an effective protector of the amine function of thymidine derivatives 2a and b , has proven to be photoremovable. This photoreaction was successfully used in the synthesis of new 5′‐amino analogs of 3′‐azido‐3′‐deoxythymidine (AZT), 6a and b . Selective photohydrolysis of 5′ N ‐tosylamides 2a and b was carried out by UV irradiation (>300 nm) in aqueous acetonitrile in the presence of 1,5‐dimethoxynaphthalene as an electron donor. © 1998 John Wiley & Sons, Ltd.