PHOTOCHEMICAL REMOVAL OF THE TOSYL GROUP FROM THE 5'N POSITION OF 5'-AMINOPYRIMIDINE NUCLEOSIDES - SYNTHETIC APPLICATIONS

Authors
URJASZ W CELEWICZ L
Citation
W. Urjasz et L. Celewicz, PHOTOCHEMICAL REMOVAL OF THE TOSYL GROUP FROM THE 5'N POSITION OF 5'-AMINOPYRIMIDINE NUCLEOSIDES - SYNTHETIC APPLICATIONS, Journal of physical organic chemistry, 11(8-9), 1998, pp. 618-621
Citations number
12
Categorie Soggetti
Chemistry Physical","Chemistry Inorganic & Nuclear
Journal title
Journal of physical organic chemistry → ACNP
ISSN journal
08943230
Volume
11
Issue
8-9
Year of publication
1998
Pages
618 - 621
Database
ISI
SICI code
0894-3230(1998)11:8-9<618:PROTTG>2.0.ZU;2-H
Abstract
The p-toluenesulfonyl (tosyl) group, an effective protector of the ami ne function of thymidine derivatives 2a and b, has proven to be photor emovable. This photoreaction was successfully used in the synthesis of new 5'-amino analogs of 3'-azido-3'-deoxythymidine (AZT), 6a and b. S elective photohydrolysis of 5'N-tosylamides 2a and b was carried out b y UV irradiation (>300 m) in aqueous acetonitrile in the presence of 1 ,5-dimethoxynaphthalene as an electron donor. (C) 1998 John Wiley & So ns, Ltd.