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Photochemical removal of the tosyl group from the 5′N position of 5′-aminopyrimidine nucleosides: syntheticapplications

✍ Scribed by Wojciech Urjasz; Lech Celewicz

Publisher: John Wiley and Sons
Year: 1998
Tongue: English
Weight: 104 KB
Volume: 11
Category: Article
ISSN: 0894-3230
DOI: 10.1002/(sici)1099-1395(199808/09)11:8/9<618::aid-poc52>3.0.co;2-f

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✦ Synopsis

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 (b300 nm) in aqueous acetonitrile in the presence of 1,5dimethoxynaphthalene as an electron donor.

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