Sulfoxide-metal exchange for the synthesis of the 2'-tributylstannyl derivative of 2',3'-didehydro-2',3'-dideoxyuridine (d4u): a general entry to 2'-carbon-substituted analogues of d4U.
Methods are described for the synthesis of the 2'-tributylstannyl derivative of 2',3'-didehydro-2',3'-dideoxyuridine (d4U). Two approaches were investigated: radical-mediated desulfonylative stannylation of the 2'-benzenesulfonyl derivative of d4U and sulfoxide-metal exchange reaction of the 2'-benzenesulfinyl derivative. The latter approach was found to give the desired 2'-stannyl derivative in good yield. It was also shown that manipulations of the stannyl group allowed the introduction of a variety of carbon-substituents to the 2'-position by applying the Stille reaction. The whole reaction sequence has opened up a highly general entry to 2'-carbon-substituted analogues of d4U.
Kumamoto
Hiroki
H
School of Pharmaceutical Sciences, Showa University, Tokyo, Japan.
Onuma
Sayoko
S
Tsuchiya
Kumiko
K
Egusa
Yuko
Y
Tanaka
Hiromichi
H
Satoh
Tsuyoshi
T
D019380:Anti-HIV Agents / Q000138:chemical synthesis*; D015224:Dideoxynucleosides / Q000138:chemical synthesis*; D008670:Metals / Q000737:chemistry; D008956:Models, Chemical; D011741:Pyrimidine Nucleosides / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013454:Sulfoxides / Q000737:chemistry; D014529:Uridine / Q000138:chemical synthesis*
D019380:Anti-HIV Agents; D015224:Dideoxynucleosides; D008670:Metals; D011741:Pyrimidine Nucleosides; D013454:Sulfoxides; C058925:2',3'-didehydro-2',3'-dideoxyuridine; D014529:Uridine