【结 构 式】 |
【分子编号】52394 【品名】[5-(2,3-bis{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}propyl)-2-[(6-{2-[5-(3-hydroxypropyl)-3-methylidenetetrahydro-2-furanyl]ethyl}-4-methyl-3-methylidenetetrahydro-2H-pyran-2-yl)methyl]-4-(methyloxy)tetrahydro-3-furanyl]methyl 4-methylbenzenesulfonate 【CA登记号】 |
【 分 子 式 】C46H80O10SSi2 【 分 子 量 】881.3722 【元素组成】C 62.69% H 9.15% O 18.15% S 3.64% Si 6.37% |
合成路线1
该中间体在本合成路线中的序号:(XXXI)Alcohol (XXIX) was converted to the corresponding tosylate (XXX) employing p-toluenesulfonyl chloride and pyridine. Replacement of the pivaloyl protecting group of (XXX) for a mono-methoxytrityl group, yielding (XXXII), was effected by reductive cleavage of the pivaloyl ester of (XXX) and then treatment of alcohol (XXXI) with methoxytrityl chloride. Displacement of the tosylate group of (XXXII) by NaI in refluxing acetone provided the alkyl iodide (XXXIII).
【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 |
---|---|---|---|---|---|---|
(XXIX) | 52392 | 3-{5-[2-(6-{[5-(2,3-bis{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}propyl)-3-(hydroxymethyl)-4-(methyloxy)tetrahydro-2-furanyl]methyl}-4-methyl-5-methylidenetetrahydro-2H-pyran-2-yl)ethyl]-4-methylidenetetrahydro-2-furanyl}propyl 2,2-dimethylpropanoate | C44H82O9Si2 | 详情 | 详情 | |
(XXX) | 52393 | 3-{(2S,5S)-5-[2-((2S,4R,6R)-6-{[(2S,3R,4R,5R)-5-((2S)-2,3-bis{[tert-butyl(dimethyl)silyl]oxy}propyl)-4-methoxy-3-({[(4-methylphenyl)sulfonyl]oxy}methyl)tetrahydro-2-furanyl]methyl}-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl]-4-methylenetetrahydro-2-furanyl}propyl 2,2-dimethylpropanoate | C51H88O11SSi2 | 详情 | 详情 | |
(XXXI) | 52394 | [5-(2,3-bis{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}propyl)-2-[(6-{2-[5-(3-hydroxypropyl)-3-methylidenetetrahydro-2-furanyl]ethyl}-4-methyl-3-methylidenetetrahydro-2H-pyran-2-yl)methyl]-4-(methyloxy)tetrahydro-3-furanyl]methyl 4-methylbenzenesulfonate | C46H80O10SSi2 | 详情 | 详情 | |
(XXXII) | 52395 | C66H96O11SSi2 | 详情 | 详情 | ||
(XXXIII) | 52396 | C59H89IO8Si2 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号:(XXXI)Alcohol (XXIX) was converted to the corresponding tosylate (XXX) employing p-toluenesulfonyl chloride and pyridine. Replacement of the pivaloyl protecting group of (XXX) for a mono-methoxytrityl group, yielding (XXXII), was effected by reductive cleavage of the pivaloyl ester of (XXX) and then treatment of alcohol (XXXI) with methoxytrityl chloride. Displacement of the tosylate group of (XXXII) by NaI in refluxing acetone provided the alkyl iodide (XXXIII).
【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 |
---|---|---|---|---|---|---|
(XXIX) | 52392 | 3-{5-[2-(6-{[5-(2,3-bis{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}propyl)-3-(hydroxymethyl)-4-(methyloxy)tetrahydro-2-furanyl]methyl}-4-methyl-5-methylidenetetrahydro-2H-pyran-2-yl)ethyl]-4-methylidenetetrahydro-2-furanyl}propyl 2,2-dimethylpropanoate | C44H82O9Si2 | 详情 | 详情 | |
(XXX) | 52393 | 3-{(2S,5S)-5-[2-((2S,4R,6R)-6-{[(2S,3R,4R,5R)-5-((2S)-2,3-bis{[tert-butyl(dimethyl)silyl]oxy}propyl)-4-methoxy-3-({[(4-methylphenyl)sulfonyl]oxy}methyl)tetrahydro-2-furanyl]methyl}-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl]-4-methylenetetrahydro-2-furanyl}propyl 2,2-dimethylpropanoate | C51H88O11SSi2 | 详情 | 详情 | |
(XXXI) | 52394 | [5-(2,3-bis{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}propyl)-2-[(6-{2-[5-(3-hydroxypropyl)-3-methylidenetetrahydro-2-furanyl]ethyl}-4-methyl-3-methylidenetetrahydro-2H-pyran-2-yl)methyl]-4-(methyloxy)tetrahydro-3-furanyl]methyl 4-methylbenzenesulfonate | C46H80O10SSi2 | 详情 | 详情 | |
(XXXII) | 52395 | C66H96O11SSi2 | 详情 | 详情 | ||
(XXXIII) | 52396 | C59H89IO8Si2 | 详情 | 详情 |