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General syntheses of 2', 3'-dideoxynucleosides and 2', 3'-didehydro-2', 3'-dideoxynucleosides

…, Y Kosugi, KC Pullaiah, P Van Roey

文献索引：Chu; Bhadti; Doboszewski; Gu; Kosugi; Pullaiah; Van Roey Journal of Organic Chemistry, 1989 ,  vol. 54,  # 9  p. 2217 - 2225

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被引用次数: 142

摘要

A general synthetic method for 2', 3'-unsaturated nucleosides from the corresponding ribonucleosides is described. The 5'-0-silyl protected ribonucleosides were converted to the bisxanthates by reaction with carbon disulfide, followed by alkylation. The bisxanthates on reduction with tri-n-butyltin hydride and deprotection of the 5'-O-silyl group afforded the unsaturated nucleosides. The desulfurization of cyclic thionocarbonates has also been ...

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1-(5-O-tert-butyldimethylsilyl-2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)thymine结构式

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1-(5-O-tert-butyldimethylsilyl-2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)thymine结构式

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1-(5-O-tert-butyldimethylsilyl-2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)thymine结构式

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5'-O-(tert-butyldimethylsilyl)-N2-isobutyryl-2',3'-O-thionocarbonylguanosine结构式

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N2-isobutyryl-2',3'-didehydro-2',3'-dideoxyguanosine结构式

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5'-O-(tert-butyldimethylsilyl)-N2-isobutyryl-2',3'-bis-O-[(methylthio)thiocarbonyl]guanosine结构式

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5'-O-(tert-buty...

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N2-isobutyryl-2',3'-didehydro-2',3'-dideoxyguanosine结构式

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5'-O-(tert-butyldimethylsilyl)-N2-isobutyryl-2',3'-bis-O-[[(β-cyanoethyl)thio]thiocarbonyl]guanosine结构式

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5'-O-(tert-buty...

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5'-O-(tert-buty...

~89%

1-((2R,5S)-5-((tert-butyldimethylsilyloxy)methyl)-2,5-dihydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione结构式

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