(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetoxy)-2-(benzoyloxy)-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9-[(triethylsilyl)oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-15-yl (4S,5R)-2,4-diphenyl-4,5-dihydro-1,3-oxazole-5-carboxylate -Drug Synthesis Database

【结构式】

【分子编号】10598

【品名】(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetoxy)-2-(benzoyloxy)-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9-[(triethylsilyl)oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-15-yl (4S,5R)-2,4-diphenyl-4,5-dihydro-1,3-oxazole-5-carboxylate

【CA登记号】

【分子式】C₅₃H₆₃NO₁₃Si

【分子量】950.16766

【元素组成】C 67% H 6.68% N 1.47% O 21.89% Si 2.96%

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)

A new synthesis of paclitaxel starting from baccatin (III) has been described: The esterification of 7-O-(triethylsilyl)baccatin III (I) with (4S,5R)-2,4-diphenyl-2-oxazoline-5-carboxylic acid (II) by means of dicyclohexylcarbodiimide (DCC) and 4-(4-pyrrolidinyl)pyridine (PPyr) in dry toluene gives the intermediate ester (III), which is then hydrolyzed with diluted HCl.

参考文献中间体

合成目标

【1】 Chaudhary, A.G.; Kingston, D.G.I.; Middleton, M.; Gunatilaka, A.K.L.; Synthesis of taxol from baccatin III via an oxazoline intermediate. Tetrahedron Lett 1994, 35, 26, 4483.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	10473	(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetoxy)-1,15-dihydroxy-10,14,17,17-tetramethyl-11-oxo-9-[(triethylsilyl)oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate	C₃₇H₅₂O₁₁Si	详情	详情
(II)	10597	(4S,5R)-2,4-Diphenyl-4,5-dihydro-1,3-oxazole-5-carboxylic acid	C₁₆H₁₃NO₃	详情	详情
(III)	10598	(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetoxy)-2-(benzoyloxy)-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9-[(triethylsilyl)oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-15-yl (4S,5R)-2,4-diphenyl-4,5-dihydro-1,3-oxazole-5-carboxylate	C₅₃H₆₃NO₁₃Si	详情	详情

Extended Information