• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【药物名称】

【化学名称】[2aR,4S,4aS,6R,9S(alphaR,betaS),11S,12S,12aR,12bS]-beta-(Benzoylamino)-alpha-hydroxybenzenepropanoic acid 12b-(acetoxy)-12-(benzoyloxy)-6-[2-[3H]-3-[3-(benzoyl)phenyl]propanoyloxy]-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-4,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-7,11-methano-1H-cyclodeca[3,4]benz[1,2-b]oxet-9-yl ester

【CA登记号】

【 分 子 式 】C61H61NO15

【 分 子 量 】1048.16402

【开发单位】State University of New York,Stony Brook (Originator)

【药理作用】Oncolytic Drugs, Taxanes

合成路线1

Selective protection of the 7-hydroxyl group of deacetylbaccatin (I) with triethylsilyl chloride provided silyl ether (II), which was acylated at position 10 with the activated ester (III) in the presence of lithium hexamethyldisilazide to give the benzoylcinnamic ester (IV). Further coupling of (IV) with beta-lactam (V) gave (VI), which by removal of the silyl groups with HF in pyridine-acetonitrile afforded (VII). The Boc group of (VII) was then removed with trifluoroacetic acid to give amine (VIII).

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) 25341 3-(3,4-dimethoxyphenyl)-1-(3-hydroxyphenyl)-1-propanone C17H18O4 详情 详情
(III) 25344 2-[[(E)-3-(3-benzoylphenyl)-2-propenoyl]oxy]-1H-isoindole-1,3(2H)-dione C24H15NO5 详情 详情
(IV) 25345 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetoxy)-12-[[(E)-3-(3-benzoylphenyl)-2-propenoyl]oxy]-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 C51H60O12Si 详情 详情
(V) 25333 tert-butyl (3R,4S)-2-oxo-4-phenyl-3-[(triisopropylsilyl)oxy]-1-azetidinecarboxylate C23H37NO4Si 详情 详情
(VI) 25346 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetoxy)-12-[[(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-9-[(triethylsilyl)oxy] C74H97NO16Si2 详情 详情
(VII) 25347 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetoxy)-12-[[(E)-3-(3-benzoylphenyl)-2-propenoyl]oxy]-15-([(2R,3S)-3-[(tert-butoxycarbonyl)amino]-2-hydroxy-3-phenylpropanoyl]oxy)-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0(3,10).0(4, C59H63NO16 详情 详情
(VIII) 25382 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetoxy)-15-[[(2R,3S)-3-amino-2-hydroxy-3-phenylpropanoyl]oxy]-12-[[(E)-3-(3-benzoylphenyl)-2-propenoyl]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 C54H55NO14 详情 详情

合成路线2

The Boc group of (VII) was then removed with trifluoroacetic acid to give amine (VIII). Then, benzoylation of the amino group of (VIII) provided benzamide (IX). Finally, hydrogenation of the cinnamyl double bond of (IX) in the presence of Wilkinson's catalyst furnished the target compound.

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
(VIII) 25382 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetoxy)-15-[[(2R,3S)-3-amino-2-hydroxy-3-phenylpropanoyl]oxy]-12-[[(E)-3-(3-benzoylphenyl)-2-propenoyl]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 C54H55NO14 详情 详情
(IX) 25383 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetoxy)-15-[[(2R,3S)-3-(benzoylamino)-2-hydroxy-3-phenylpropanoyl]oxy]-12-[[(E)-3-(3-benzoylphenyl)-2-propenoyl]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 benzoate C61H59NO15 详情 详情
Extended Information