(2S,3R,4S,5R)-2-([(2S,3R,4R,5S)-3-(acetoxy)-2-([(3S,10R,13S,16S,17S)-3-[[tert-butyl(dimethyl)silyl]oxy]-17-hydroxy-17-[(1S)-1-(2-isopentyl-1,3-dioxolan-2-yl)ethyl]-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-16-yl]oxy)-5-[(triethylsilyl)oxy]tetrahydro-2H-pyran-4-yl]oxy)-4,5-bis[(4-methoxybenzyl)oxy]tetrahydro-2H-pyran-3-yl 4-methoxybenzoate -Drug Synthesis Database

【结构式】

【分子编号】48965

【品名】(2S,3R,4S,5R)-2-([(2S,3R,4R,5S)-3-(acetoxy)-2-([(3S,10R,13S,16S,17S)-3-[[tert-butyl(dimethyl)silyl]oxy]-17-hydroxy-17-[(1S)-1-(2-isopentyl-1,3-dioxolan-2-yl)ethyl]-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-16-yl]oxy)-5-[(triethylsilyl)oxy]tetrahydro-2H-pyran-4-yl]oxy)-4,5-bis[(4-methoxybenzyl)oxy]tetrahydro-2H-pyran-3-yl 4-methoxybenzoate

【CA登记号】

【分子式】C₇₇H₁₁₆O₁₈Si₂

【分子量】1385.92824

【元素组成】C 66.73% H 8.44% O 20.78% Si 4.05%

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：(XXXVII)

Final assembly of the target compound: The condensation of the intermediate aglycon (XXXVI) with the intermediate disaccharide (XX) by means of Tms-OTf in dichloromethane gives the protected adduct (XXXVII), which is finally treated first with DDQ and then with Pd(MeCN)2Cl2 in acetone/water to obtain the target saponin, OSW-1.

参考文献中间体

合成目标

【1】 Jin, Z.; Yu, W.; A new strategy for the stereoselective introduction of steroid side chain via alpha-alkoxy vinyl cuprates: Total synthesis of a highly potent antitumor natural product OSW-1. J Am Chem Soc 2001, 123, 14, 3369.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(XX)	48952	(2S,3R,4S,5R)-2-([(3R,4R,5S)-3-(acetoxy)-2-[(2,2,2-trichloroethanimidoyl)oxy]-5-[(triethylsilyl)oxy]tetrahydro-2H-pyran-4-yl]oxy)-4,5-bis[(4-methoxybenzyl)oxy]tetrahydro-2H-pyran-3-yl 4-methoxybenzoate	C₄₄H₅₆Cl₃NO₁₄Si	详情	详情
(XXXVI)	48964	(3S,10R,13S,16S,17S)-3-[[tert-butyl(dimethyl)silyl]oxy]-17-[(1S)-1-(2-isopentyl-1,3-dioxolan-2-yl)ethyl]-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-16,17-diol	C₃₅H₆₂O₅Si	详情	详情
(XXXVII)	48965	(2S,3R,4S,5R)-2-([(2S,3R,4R,5S)-3-(acetoxy)-2-([(3S,10R,13S,16S,17S)-3-[[tert-butyl(dimethyl)silyl]oxy]-17-hydroxy-17-[(1S)-1-(2-isopentyl-1,3-dioxolan-2-yl)ethyl]-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-16-yl]oxy)-5-[(triethylsilyl)oxy]tetrahydro-2H-pyran-4-yl]oxy)-4,5-bis[(4-methoxybenzyl)oxy]tetrahydro-2H-pyran-3-yl 4-methoxybenzoate	C₇₇H₁₁₆O₁₈Si₂	详情	详情

Extended Information