Application Of the Michaelis-Arbuzov Reaction to the Synthesis Of Internucleoside 3'-S-Phosphorothiolate Linkages
Data(s) |
01/08/1994
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Resumo |
The 5'-O-monomethoxytrityl-3'-S-(aryldisulfanyl)-3'-deoxythymidines 7 and 8 have been prepared by the reaction of 5'-O-monomethoxytrityl-3'-thiothymidine with the appropriate arenesulfenyl chloride. These disulfides undergo a Michaelis–Arbusov reaction with simple trialkyl phosphites to yield 5'-O-monomethoxytrityl-3'-thiothymidin-3'-yl O,O-dialkyl phosphorothiolates. More interestingly, 3'-deoxy-3'-S-(2, 4-dinitrophenylsulfanyl)-5'-O-monomethoxytritylthymidine 8 reacts with a variety of thymidin-5'-yl dialkyl phosphites to give dithymidine phosphorothiolate triesters with the phosphorothiolate group protected with either a methyl or a 2-cyanoethyl group. 3'-O-(tert-Butyldimethylsilyl)thymidin-5'-yl triethylammoniumphosphonate 17 is converted into the corresponding bis-(O-trimethylsilyl) phosphite by treatment with bis(trimethylsilyl)trifluoroacetamide. in situ Reaction of this phosphate with disulfide 8 gives, after work-up, the dithymidine phosphorothiolate diester directly. Methylation of compound 17 with methyl chloromethanoate, followed by silylation and subsequent reaction with disulfide 8, gives the methyl-protected dithymidine phosphorothiolate triester. |
Identificador | |
Idioma(s) |
eng |
Direitos |
info:eu-repo/semantics/restrictedAccess |
Fonte |
Li , X , Scott , G K , Baxter , A D , Vyle , J , Taylor , R J & Cosstick , R 1994 , ' Application Of the Michaelis-Arbuzov Reaction to the Synthesis Of Internucleoside 3'-S-Phosphorothiolate Linkages ' Journal of the Chemical Society - Perkin Transactions 1 , vol (15) , pp. 2123-2129 . DOI: 10.1039/p19940002123 |
Tipo |
article |