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【结 构 式】

【分子编号】42578

【品名】(5S)-5-([[tert-butyl(diphenyl)silyl]oxy]methyl)-3,3-bis(phenylsulfanyl)dihydro-2(3H)-furanone

【CA登记号】

【 分 子 式 】C33H34O3S2Si

【 分 子 量 】570.84866

【元素组成】C 69.43% H 6% O 8.41% S 11.23% Si 4.92%

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:(III)

The reaction of gamma-lactone (I) with N-(phenylsulfanyl)phthalimide (II) by means of LiHMDS in THF gives the 2,2-bis(phenylsulfanyl)lactone (III), which is reduced with DIBAL in THF to yield 5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2,2-bis(phenylsulfanyl)-D-ribose (IV). The reaction of (IV) with acetic anhydride affords the acetylated ribose (V), which is condensed with bis(trimethylsilyl)thymine (VI) by means of TMS-OTf in acetonitrile to provide the glycosylated thymine (VII). The oxidation of (VII) with 1 mol of MCPBA in dichloromethane gives the sulfinyl compound (VIII), which is treated with tributylamine in refluxing xylene to yield the 2',3'-didehydro compound (IX). The oxidation of (IX) with MCPBA in dichloromethane gives the phenylsulfonyl derivative (X), which is desulfurized with sodium amalgam in methanol, yielding the silylated intermediate (XI). Finally, this compound is desilylated with TBAF in THF.

1 Kawakami, H.; et al.; Condensation reaction between 2,2-diphenylthio-2,3-dideoxyriboside and silyvated pyrimidine bases. Nucleosides Nucleotides 1992, 11, 9, 1673.
2 Ebata, T.; Matsushita, H.; Kuno, H.; Niihata, S.; Synthesis of 2',3'-didehydro-2',3'-dideoxy nucleosides from 2',2'-bis (phenylthio) nucleoside analogs. Bull Chem Soc Jpn 1995, 68, 8, 2327.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 12215 (5S)-5-([[tert-Butyl(diphenyl)silyl]oxy]methyl)dihydro-2(3H)-furanone C21H26O3Si 详情 详情
(II) 42577 2-(phenylsulfanyl)-1H-isoindole-1,3(2H)-dione 14204-27-4 C14H9NO2S 详情 详情
(III) 42578 (5S)-5-([[tert-butyl(diphenyl)silyl]oxy]methyl)-3,3-bis(phenylsulfanyl)dihydro-2(3H)-furanone C33H34O3S2Si 详情 详情
(IV) 42579 (5S)-5-([[tert-butyl(diphenyl)silyl]oxy]methyl)-3,3-bis(phenylsulfanyl)tetrahydro-2-furanol C33H36O3S2Si 详情 详情
(V) 42580 (5S)-5-([[tert-butyl(diphenyl)silyl]oxy]methyl)-3,3-bis(phenylsulfanyl)tetrahydro-2-furanyl acetate C35H38O4S2Si 详情 详情
(VI) 41900 5-methyl-2,4-bis[(trimethylsilyl)oxy]pyrimidine; 5-methyl-2-[(trimethylsilyl)oxy]-4-pyrimidinyl trimethylsilyl ether 7288-28-0 C11H22N2O2Si2 详情 详情
(VII) 42584 1-[(2S,5S)-5-([[tert-butyl(diphenyl)silyl]oxy]methyl)-3,3-bis(phenylsulfanyl)tetrahydro-2-furanyl]-5-methyl-2,4(1H,3H)-pyrimidinedione C38H40N2O4S2Si 详情 详情
(VIII) 42581 1-[(2R,5S)-5-([[tert-butyl(diphenyl)silyl]oxy]methyl)-3-(phenylsulfanyl)-3-(phenylsulfinyl)tetrahydro-2-furanyl]-5-methyl-2,4(1H,3H)-pyrimidinedione C38H40N2O5S2Si 详情 详情
(IX) 42582 1-[(2R,5S)-5-([[tert-butyl(diphenyl)silyl]oxy]methyl)-3-(phenylsulfanyl)-2,5-dihydro-2-furanyl]-5-methyl-2,4(1H,3H)-pyrimidinedione C32H34N2O4SSi 详情 详情
(X) 42583 1-[(2R,5S)-5-([[tert-butyl(diphenyl)silyl]oxy]methyl)-3-(phenylsulfonyl)-2,5-dihydro-2-furanyl]-5-methyl-2,4(1H,3H)-pyrimidinedione C32H34N2O6SSi 详情 详情
(XI) 12223 1-[(2R,5S)-5-([[tert-Butyl(diphenyl)silyl]oxy]methyl)-2,5-dihydro-2-furanyl]-5-methyl-2,4(1H,3H)-pyrimidinedione C26H30N2O4Si 详情 详情
Extended Information