Lithiation study on D4T.
Upon treatment with LTMP, 5'-O-protected D4T undergoes deprotonation of the vinylic proton (H-3' or H-2'): when 5'-O-silyl derivative was used, the 3'-C-silylated product was formed as a result of C3'-lithiation and subsequent O-->C silyl migration, while deprotonation at the 2'-position led to the formation of an allene derivative. A stannyl version of this reaction was also examined to develop a method for C3'-functionalization of D4T.
Kumamoto
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School of Pharmaceutical Sciences, Showa University, 1-5-8 Hatanodai, Shinagawa-ku, Tokyo 142-8555, Japan.
Tanaka
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D008094:Lithium / Q000737:chemistry; D008722:Methods; D015394:Molecular Structure; D018119:Stavudine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
D008094:Lithium; D018119:Stavudine