SYNTHESES OF 2'-DEOXYPSEUDOURIDINE, 2'-DEOXYFORMYCIN-B, AND 2',3'-DIDEOXYFORMYCIN-B BY PALLADIUM-MEDIATED GLYCAL AGLYCON COUPLING
SYNTHESES OF 2'-DEOXYPSEUDOURIDINE, 2'-DEOXYFORMYCIN-B, AND 2',3'-DIDEOXYFORMYCIN-B BY PALLADIUM-MEDIATED GLYCAL AGLYCON COUPLING
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DOI：
10.1021/jo00043a029
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发表时间：
1992-08-01
影响因子：
3.6
通讯作者：
DAVES, GD
中科院分区：
文献类型：
--
作者：
ZHANG, HC;DAVES, GD
5-Iodouracil and the ribofuranoid glycal 1,4-anhydro-2-deoxy-3-O-[(1,1-dimethylethyl)diphenylsilyl]-D-erythro-pent-1-enitol underwent regio- and stereospecific coupling in the presence of catalytic palladium acetate and either triphenylphosphine or triphenylarsine ligands. The resulting C-glycosyl product was converted to 2'-deoxypseudouridine, 5-(2'-deoxy-beta-D-ribofuranosyl)-2,4(1H,3H)-pyrimidinedione (63% overall yield). In a similar way, 2'-deoxyformycin B, 3-(2'-deoxy-beta-D-ribofuranosyl)pyrazolo[4,3-d]pyrimidin-7-one, and 2,3'-dideoxyformycin B, 3-(2',3'-dideoxy-beta-D-ribofuranosyl)pyrazolo[4,3-d]pyrimidin-7-one, have been synthesized by reaction sequences in which the key step is a palladium-mediated regio- and stereospecific C-glycosyl bond forming reaction between this furanoid glycal and a bis(tetrahydropyranyl)-protected 3-iodopyrazolo[4,3-d]pyrimidine aglycon derivative.
