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【结 构 式】 
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【分子编号】25382 【品名】(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 【CA登记号】 |
【 分 子 式 】C54H55NO14 【 分 子 量 】942.02904 【元素组成】C 68.85% H 5.88% N 1.49% O 23.78% |
合成路线1
该中间体在本合成路线中的序号：(VIII)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
该中间体在本合成路线中的序号：(VIII)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 |