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

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.

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