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Photochemical removal of the tosyl group from the 5′N position of 5′-aminopyrimidine nucleosides: syntheticapplications (1998)

Urjasz, Wojciech ; Celewicz, Lech

Chichester : Wiley-Blackwell

Journal of Physical Organic Chemistry 11 (1998), S. 618-621

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ISSN: 0894-3230

Keywords: 5′-aminopyrimidines ; p-toluenesulfonyl photoremoval ; 3′-azido-3′-deoxythymidine derivatives ; Chemistry ; Theoretical, Physical and Computational Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology , Physics

Notes: 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.

Additional Material: 3 Ill.

Type of Medium: Electronic Resource

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