(3S,6R,7S,8S)-11-[(2R,3S)-3-[(2S,3E)-2-azido-3-methyl-4-(2-methyl-1,3-thiazol-4-yl)-3-butenyl]-2-methyloxiranyl]-3,7-dihydroxy-4,4,6,8-tetramethyl-5-oxoundecanoic acid -Drug Synthesis Database

【结构式】

【分子编号】47825

【品名】(3S,6R,7S,8S)-11-[(2R,3S)-3-[(2S,3E)-2-azido-3-methyl-4-(2-methyl-1,3-thiazol-4-yl)-3-butenyl]-2-methyloxiranyl]-3,7-dihydroxy-4,4,6,8-tetramethyl-5-oxoundecanoic acid

【CA登记号】

【分子式】C₂₇H₄₂N₄O₆S

【分子量】550.71984

【元素组成】C 58.89% H 7.69% N 10.17% O 17.43% S 5.82%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(II)

The cleavage of the lactone group of epothilone B (I) by means of Na-N3 and tetrakis triphenylphosphine palladium (0) in THF gives the azido carboxylic acid (II), which is reduced with polymer-supported PPH3 (or in solution) or with H2 over PtO2 in ethanol to yield the amino acid (III). Finally, this compound is cyclized by means of diphenylphosphoryl azide (DPPA) in DMF.

参考文献中间体

合成目标

【2】 Vite, G.D.; Kim, S.-H.; Johnson, J.A.; Borzilleri, R.M. (Bristol-Myers Squibb Co.); Epothilone derivs.. WO 9902514 .
【3】 Borzilleri, R.M.; Soong-Hoon, K. (Bristol-Myers Squibb Co.); A process for the preparation of ring-opened epothilone intermediates which are useful for the preparation of epothilone analogs. WO 9927890 .
【1】 Borzilleri, R.M.; Zheng, X.; Schmidt, R.J.; et al.; A novel application of a Pd(0)-catalyzed nucleophilic substitution reaction to the regio- and stereoselective synthesis of lactam analogues of the epothilone natural products. J Am Chem Soc 2000, 122, 37, 8890.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	42208	(1S,3S,7S,10R,11S,12S,16R)-7,11-dihydroxy-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	C₂₇H₄₁NO₆S	详情	详情
(II)	47825	(3S,6R,7S,8S)-11-[(2R,3S)-3-[(2S,3E)-2-azido-3-methyl-4-(2-methyl-1,3-thiazol-4-yl)-3-butenyl]-2-methyloxiranyl]-3,7-dihydroxy-4,4,6,8-tetramethyl-5-oxoundecanoic acid	C₂₇H₄₂N₄O₆S	详情	详情
(III)	47826	(3S,6R,7S,8S)-11-[(2R,3S)-3-[(2S,3E)-2-amino-3-methyl-4-(2-methyl-1,3-thiazol-4-yl)-3-butenyl]-2-methyloxiranyl]-3,7-dihydroxy-4,4,6,8-tetramethyl-5-oxoundecanoic acid	C₂₇H₄₄N₂O₆S	详情	详情

合成路线2

该中间体在本合成路线中的序号：(II)

参考文献中间体

合成目标

【1】 Borzilleri RM, Zheng X, Schmidt RJ, et al. 2000. A novel applicant pf a Pd(0)-catalyzed nucleophilic substitution reaction to the regio-and stereoselective synthesis of lactam analogues of the Epothilone natural products. J Am Chem Soc, 122: 8890～8897.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	42208	(1S,3S,7S,10R,11S,12S,16R)-7,11-dihydroxy-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	C₂₇H₄₁NO₆S	详情	详情
(II)	47825	(3S,6R,7S,8S)-11-[(2R,3S)-3-[(2S,3E)-2-azido-3-methyl-4-(2-methyl-1,3-thiazol-4-yl)-3-butenyl]-2-methyloxiranyl]-3,7-dihydroxy-4,4,6,8-tetramethyl-5-oxoundecanoic acid	C₂₇H₄₂N₄O₆S	详情	详情
(III)	47826	(3S,6R,7S,8S)-11-[(2R,3S)-3-[(2S,3E)-2-amino-3-methyl-4-(2-methyl-1,3-thiazol-4-yl)-3-butenyl]-2-methyloxiranyl]-3,7-dihydroxy-4,4,6,8-tetramethyl-5-oxoundecanoic acid	C₂₇H₄₄N₂O₆S	详情	详情

Extended Information