【结 构 式】 |
【分子编号】41096 【品名】(1S,2S,3R,4S,7R,9S,10S,12R,15S)-12-(acetoxy)-1-[(dimethylsilyl)oxy]-4-hydroxy-10,14,17,17-tetramethyl-11-oxo-9,15-bis[(triethylsilyl)oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate 【CA登记号】 |
【 分 子 式 】C43H70O10Si3 【 分 子 量 】831.2793 【元素组成】C 62.13% H 8.49% O 19.25% Si 10.14% |
合成路线1
该中间体在本合成路线中的序号:(I)The silyl-protected 4-deacetyl baccatin (I) was deprotonated with lithium bis(trimethylsilyl) amide and then condensed with methyl chloroformate to produce carbonate (II). Desilylation of (II) using HF in pyridine afforded triol (III), which was selectively resilylated at the 7-hydroxyl group to furnish (IV). Attachment of the C-13 side-chain of (IV) was achieved by treatment with lactam (V) and lithium bis(trimethylsilyl)amide, yielding ester (VI). Finally, the silyl protecting groups of (VI) were removed by treatment with HF in pyridine.
【1】 Long, B.H.; Chen, S.H.; Wei, J.-M.; et al.; Novel C-4 paclitaxel (Taxol) analogs: Potent antitumor agents. Bioorg Med Chem Lett 1995, 5, 22, 2741. |
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) | 41096 | (1S,2S,3R,4S,7R,9S,10S,12R,15S)-12-(acetoxy)-1-[(dimethylsilyl)oxy]-4-hydroxy-10,14,17,17-tetramethyl-11-oxo-9,15-bis[(triethylsilyl)oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate | C43H70O10Si3 | 详情 | 详情 | |
(II) | 41097 | (1S,2S,3R,4S,7R,9S,10S,12R,15S)-12-(acetoxy)-1-[(dimethylsilyl)oxy]-4-[(methoxycarbonyl)oxy]-10,14,17,17-tetramethyl-11-oxo-9,15-bis[(triethylsilyl)oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate | C45H72O12Si3 | 详情 | 详情 | |
(III) | 41098 | (1S,2S,3R,4S,7R,9S,10S,12R,15S)-12-(acetoxy)-1,9,15-trihydroxy-4-[(methoxycarbonyl)oxy]-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate | C31H38O12 | 详情 | 详情 | |
(IV) | 41099 | (1S,2S,3R,4S,7R,9S,10S,12R,15S)-12-(acetoxy)-1,15-dihydroxy-4-[(methoxycarbonyl)oxy]-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 | C37H52O12Si | 详情 | 详情 | |
(V) | 10490 | (3R,4S)-1-Benzoyl-4-phenyl-3-[(triethylsilyl)oxy]-2-azetanone | C22H27NO3Si | 详情 | 详情 | |
(VI) | 41100 | C59H79NO15Si2 | 详情 | 详情 |