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
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硫氧化物-金属交换合成 2,3-二氢-2,3-二脱氧尿苷 (d4U) 的 2-三丁基甲锡烷基衍生物:2-碳取代的 d4U 类似物的一般条目

DOI:
10.1081/ncn-120006826
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发表时间:
2002
期刊:
Nucleosides, Nucleotides & Nucleic Acids
影响因子:
--
通讯作者:
T. Satoh
T. Satoh
中科院分区:
--
文献类型:
--
作者:
H. Kumamoto;Sayoko Onuma;Kumiko Tsuchiya;Yuko Egusa;Hiromichi Tanaka;T. Satoh

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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.
DOI: 10.1016/s0040-4020(98)00243-9
发表时间: 1998-05
期刊: Tetrahedron
影响因子: 2.1
作者:
T. Satoh;Koji Takano;H. Ota;H. Someya;K. Matsuda;M. Koyama
通讯作者: T. Satoh;Koji Takano;H. Ota;H. Someya;K. Matsuda;M. Koyama