1-[(2R,5S)-5-({[tert-butyl(diphenyl)silyl]oxy}methyl)-2,5-dihydro-2-furanyl]-5-fluoro-4-[(trimethylsilyl)amino]-2(1H)-pyrimidinone -Drug Synthesis Database

【结构式】

【分子编号】56707

【品名】1-[(2R,5S)-5-({[tert-butyl(diphenyl)silyl]oxy}methyl)-2,5-dihydro-2-furanyl]-5-fluoro-4-[(trimethylsilyl)amino]-2(1H)-pyrimidinone

【CA登记号】

【分子式】C₂₈H₃₆FN₃O₃Si₂

【分子量】537.7816632

【元素组成】C 62.54% H 6.75% F 3.53% N 7.81% O 8.93% Si 10.44%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(IV)

The condensation of the known acetate (I) with N,O-disylilated cytosine (II) by means of Tms-OTf or SnCl4 gives the selenium containing nucleoside (III), which is submitted to an oxidative elimination reaction by means of H2O2 and pyridine in dichloromethane to yield the unsaturated nucleoside (IV). Finally, this compound is desilylated by means of TBAF in THF.

参考文献中间体

合成目标

【1】 Shi, J.; et al.; Synthesis and biological evaluation of 2',3'-didehydro-2',3'-dideoxy-5-fluorocytidine (D4FC) analogues: Discovery of carbocyclic nucleoside triphosphates with potent inhibitory activity against HIV-1 reverse transcriptase. J Med Chem 1999, 42, 5, 859.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	12217	(3R,5S)-5-([[tert-butyl(diphenyl)silyl]oxy]methyl)-3-(phenylselanyl)tetrahydro-2-furanyl acetate	C₂₉H₃₄O₄SeSi	详情	详情
(II)	36959	5-fluoro-N-(trimethylsilyl)-2-[(trimethylsilyl)oxy]-4-pyrimidinamine; N-[5-fluoro-2-[(trimethylsilyl)oxy]-4-pyrimidinyl]-N-(trimethylsilyl)amine	C₁₀H₂₀FN₃OSi₂	详情	详情
(III)	56706	1-[(2R,3R,5S)-5-({[tert-butyl(diphenyl)silyl]oxy}methyl)-3-(phenylselanyl)tetrahydro-2-furanyl]-5-fluoro-4-[(trimethylsilyl)amino]-2(1H)-pyrimidinone	C₃₄H₄₂FN₃O₃SeSi₂	详情	详情
(IV)	56707	1-[(2R,5S)-5-({[tert-butyl(diphenyl)silyl]oxy}methyl)-2,5-dihydro-2-furanyl]-5-fluoro-4-[(trimethylsilyl)amino]-2(1H)-pyrimidinone	C₂₈H₃₆FN₃O₃Si₂	详情	详情

Extended Information