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【结 构 式】

【分子编号】60656

【品名】trityl (3S,4R,7S)-7-{[tert-butyl(dimethyl)silyl]oxy}-4,6,6-trimethyl-3-[(1S)-1-methyl-4-((2R,3S)-2-methyl-3-{(2S,3E)-3-methyl-4-(2-methyl-1,3-thiazol-4-yl)-2-[(triethylsilyl)oxy]-3-butenyl}oxiranyl)butyl]-5-oxo-9-decenoate

【CA登记号】

【 分 子 式 】C61H89NO6SSi2

【 分 子 量 】1020.6178

【元素组成】C 71.79% H 8.79% N 1.37% O 9.41% S 3.14% Si 5.5%

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:(XVIII)

The condensation of (XV) with the chiral ketone (XVI) by means of LDA in TH gives the aldol (XVII). The protection of the OH group of (XVII) with Troc-Cl and pyridine yields compound (XVIII), which is oxidized at the vinyl group by means of OsO4, NaIO4, selectively monodesilylated with HF and pyridine, and further oxidated with NaClO2 to afford the hydroxyacid (XIX). The Yamaguchi macrolactonization of (XIX) by means of 2,4,6-trichlorobenzoyl chloride provides the macrocyclic lactone (XX). Elimination of the Troc protecting group of (XX) by means of Zn and NH4Cl gives the silylated precursor (XXI), which is finally deprotected by means of HF and pyridine to yield the target epothilone B.

1 Bode, J.W.; Carreira, E.M.; Stereoselective syntheses of epothilones A and B via nitrile oxide cycloadditions and related studies. J Org Chem 2001, 66, 19, 6410.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XV) 49278 (2S)-2-methyl-5-((2R,3S)-2-methyl-3-[(2S,3E)-3-methyl-4-(2-methyl-1,3-thiazol-4-yl)-2-[(triethylsilyl)oxy]-3-butenyl]oxiranyl)pentanal C24H41NO3SSi 详情 详情
(XVI) 44451 (5S)-5-[[tert-butyl(dimethyl)silyl]oxy]-4,4-dimethyl-7-octen-3-one C16H32O2Si 详情 详情
(XVII) 49298 (4S,7R,8S,9S)-4-[[tert-butyl(dimethyl)silyl]oxy]-8-hydroxy-5,5,7,9-tetramethyl-12-((2R,3S)-2-methyl-3-[(2S,3E)-3-methyl-4-(2-methyl-1,3-thiazol-4-yl)-2-[(triethylsilyl)oxy]-3-butenyl]oxiranyl)-1-dodecen-6-one C40H73NO5SSi2 详情 详情
(XVIII) 60656 trityl (3S,4R,7S)-7-{[tert-butyl(dimethyl)silyl]oxy}-4,6,6-trimethyl-3-[(1S)-1-methyl-4-((2R,3S)-2-methyl-3-{(2S,3E)-3-methyl-4-(2-methyl-1,3-thiazol-4-yl)-2-[(triethylsilyl)oxy]-3-butenyl}oxiranyl)butyl]-5-oxo-9-decenoate C61H89NO6SSi2 详情 详情
(XIX) 60657 (3S,6R,7S,8S)-3-{[tert-butyl(dimethyl)silyl]oxy}-11-{(2R,3S)-3-[(2S,3E)-2-hydroxy-3-methyl-4-(2-methyl-1,3-thiazol-4-yl)-3-butenyl]-2-methyloxiranyl}-4,4,6,8-tetramethyl-5-oxo-7-[2-oxo-2-(trityloxy)ethyl]undecanoic acid C54H73NO8SSi 详情 详情
(XX) 60658 trityl 2-{(1S,3S,7S,10R,11S,12S,16R)-7-{[tert-butyl(dimethyl)silyl]oxy}-8,8,10,12,16-pentamethyl-3-[(E)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)ethenyl]-5,9-dioxo-4,17-dioxabicyclo[14.1.0]heptadec-11-yl}acetate C54H71NO7SSi 详情 详情
(XXI) 49303 (1S,3S,7S,10R,11S,12S,16R)-7-[[tert-butyl(dimethyl)silyl]oxy]-11-hydroxy-8,8,10,12,16-pentamethyl-3-[(E)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)ethenyl]-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione C33H55NO6SSi 详情 详情
Extended Information