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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

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

Hiroki Kumamoto, Sayoko Onuma, Kumiko Tsuchiya, Yuko Egusa, Hiromichi Tanaka, Tsuyoshi Satoh

Nucleosides Nucleotides Nucleic Acids. Apr-May 2002;21(4-5):275-86.

PMID: 12182344

Abstract:

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP1105511656	2-(Tributylstannyl)-3-methoxypyrazine		1105511-65-6	Price

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