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【结 构 式】 
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【分子编号】52424 【品名】20-(2,3-dihydroxypropyl)-14-methyl-8,15-dimethylidene-21-(methyloxy)-2,19,30,34,37,39,40,41-octaoxanonacyclo[24.9.2.1~3,32~.1~3,33~.1~6,9~.1~12,16~.0~18,22~.0~29,36~.0~31,35~]hentetracontan-24-one 【CA登记号】 |
【 分 子 式 】C40H58O12 【 分 子 量 】730.89332 【元素组成】C 65.73% H 8% O 26.27% |
合成路线1
该中间体在本合成路线中的序号：(XLVIII)Cyclization between the aldehyde and vinyl iodide moieties of (XXXVIII) was achieved by NiCl2/CrCl2-promoted intramolecular condensation. The resulting macrocyclic alcohol (XLV) was then oxidized to ketone (XLVI) with Dess-Martin periodinane reagent. Deprotection of (XLVI) with tetrabutylammonium fluoride furnished the fully desilylated compound (XLVII). Then, cyclization between hydroxyl groups and the unsaturated ketone groups of (XLVII) under acidic conditions gave rise to the polycyclic compound (XLVIII).
| 【1】 Littlefield, B.A.; Zheng, W.; Seletsky, B.M.; Yu, M.J.; Palme, M.H.; Towle, M.J. (Eisai Co., Ltd.); Macrocyclic analogs and methods of their use and preparation. US 6214865; WO 9965894 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XLVa) | 52407 | C70H132O13Si5 | 详情 | 详情 | ||
| (XLVb) | 52408 | C70H132O13Si5 | 详情 | 详情 | ||
| (XXXVIII) | 52400 | C70H131IO13Si5 | 详情 | 详情 | ||
| (XLVI) | 52409 | C70H130O13Si5 | 详情 | 详情 | ||
| (XLVII) | 52410 | C40H60O13 | 详情 | 详情 | ||
| (XLVIII) | 52424 | 20-(2,3-dihydroxypropyl)-14-methyl-8,15-dimethylidene-21-(methyloxy)-2,19,30,34,37,39,40,41-octaoxanonacyclo[24.9.2.1~3,32~.1~3,33~.1~6,9~.1~12,16~.0~18,22~.0~29,36~.0~31,35~]hentetracontan-24-one | C40H58O12 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(XLVIII)The primary hydroxyl group of diol (XLVIII) was selectively mesylated with methanesulfonyl chloride and collidine at low temperature. The resultant mesylate (IL) was then condensed with tetrabutylammonium azide in hot DMF to produce the alkyl azide (L). The azide function of (L) was finally reduced to the corresponding primary amine by treatment with trimethylphosphine in moist THF.
| 【1】 Littlefield, B.A.; Zheng, W.; Seletsky, B.M.; Yu, M.J.; Palme, M.H.; Towle, M.J. (Eisai Co., Ltd.); Macrocyclic analogs and methods of their use and preparation. US 6214865; WO 9965894 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (IL) | 52425 | C41H60O14S | 详情 | 详情 | ||
| (XLVIII) | 52424 | 20-(2,3-dihydroxypropyl)-14-methyl-8,15-dimethylidene-21-(methyloxy)-2,19,30,34,37,39,40,41-octaoxanonacyclo[24.9.2.1~3,32~.1~3,33~.1~6,9~.1~12,16~.0~18,22~.0~29,36~.0~31,35~]hentetracontan-24-one | C40H58O12 | 详情 | 详情 | |
| (L) | 52426 | C40H57N3O11 | 详情 | 详情 |