(1S,2S,3R,4S,7R,9S,10R,12R,15S)-4,12-bis(acetoxy)-15-([(2R,3S)-3-[(tert-butoxycarbonyl)amino]-3-phenyl-2-[(triisopropylsilyl)oxy]propanoyl]oxy)-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl -Drug Synthesis Database

【结构式】

【分子编号】25335

【品名】(1S,2S,3R,4S,7R,9S,10R,12R,15S)-4,12-bis(acetoxy)-15-([(2R,3S)-3-[(tert-butoxycarbonyl)amino]-3-phenyl-2-[(triisopropylsilyl)oxy]propanoyl]oxy)-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl

【CA登记号】

【分子式】C₅₄H₇₅NO₁₅Si

【分子量】1006.27274

【元素组成】C 64.46% H 7.51% N 1.39% O 23.85% Si 2.79%

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：(V)

Selective protection of the 7-hydroxyl group of deacetylbaccatin (I) with triethylsilyl chloride provided silyl ether (II), which was acetylated at position 10 using acetyl chloride and lithium hexamethyldisilazide. Further coupling of (II) with beta-lactam (III) gave (IV), which by selective removal of the 7-silyl group with 0.1 N HCl gave 10-acetyl-2'-(triisopropylsilyl)docetaxel (V). This was condensed with benzoylcinnamic acid (VI) employing EDC and DMAP to afford ester (VII).

参考文献中间体

合成目标

【1】 Ahern, D.G.; Ojima, I.; Bounaud, P.-Y.; New photoaffinity analogs of paclitaxel. Bioorg Med Chem Lett 1999, 9, 8, 1189.

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)	25331	3-hydroxyacetophenone; 1-(3-hydroxyphenyl)-1-ethanone	121-71-1	C₈H₈O₂	详情	详情
(II)	25332	(E)-3-(3,4-dimethoxyphenyl)-1-(3-hydroxyphenyl)-2-propen-1-one		C₁₇H₁₆O₄	详情	详情
(III)	25333	tert-butyl (3R,4S)-2-oxo-4-phenyl-3-[(triisopropylsilyl)oxy]-1-azetidinecarboxylate		C₂₃H₃₇NO₄Si	详情	详情
(IV)	25334	(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetoxy)-15-([(2R,3S)-3-[(tert-butoxycarbonyl)amino]-3-phenyl-2-[(triisopropylsilyl)oxy]propanoyl]oxy)-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9-[(triethylsilyl)oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]h		C₆₀H₈₉NO₁₅Si₂	详情	详情
(V)	25335	(1S,2S,3R,4S,7R,9S,10R,12R,15S)-4,12-bis(acetoxy)-15-([(2R,3S)-3-[(tert-butoxycarbonyl)amino]-3-phenyl-2-[(triisopropylsilyl)oxy]propanoyl]oxy)-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl		C₅₄H₇₅NO₁₅Si	详情	详情
(VI)	25336	(E)-3-(3-benzoylphenyl)-2-propenoic acid		C₁₆H₁₂O₃	详情	详情
(VII)	25337	(1S,2S,3R,4S,7R,9S,10R,12R,15S)-4,12-bis(acetoxy)-9-[[(E)-3-(3-benzoylphenyl)-2-propenoyl]oxy]-15-([(2R,3S)-3-[(tert-butoxycarbonyl)amino]-3-phenyl-2-[(triisopropylsilyl)oxy]propanoyl]oxy)-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[1		C₇₀H₈₅NO₁₇Si	详情	详情

Extended Information