5′-Benzoyl-2′ α-bromo-3′-O-methanesulfonylthymidine: A superior nucleoside for the synthesis of the anti-AIDS drug D4T (Stavudine)
BC Chen, SL Quinlan, DR Stark, JG Reid, VH Audia…
Index: Chen, Bang-Chi; Quinlan, Sandra L.; Stark, Derron R.; Reid, J. Gregory; Audia, Vicki H.; et al. Tetrahedron Letters, 1995 , vol. 36, # 44 p. 7957 - 7960
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Citation Number: 26
Abstract
The anti-AIDS drug d4T is prepared in 75% overall yield starting from the readily available ribonucleoside 5-methyluridine (1). The key step in this new synthesis is the zinc-induced reductive elimination of the bromomesylate 4, which affords d4T without nucleoside bond cleavage. A facile procedure for the deprotection/isolation of this highly water soluble product is also described.
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