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【结 构 式】 
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【分子编号】64634 【品名】((2R,4S,6R)-4-{[tert-butyl(dimethyl)silyl]oxy}-6-{[(4S,6S)-6-(2-{[tert-butyl(diphenyl)silyl]oxy}ethyl)-2,2-dimethyl-1,3-dioxan-4-yl]methyl}-6-methoxy-4-methyltetrahydro-2H-pyran-2-yl)methyl 4-methylbenzenesulfonate 【CA登记号】 |
【 分 子 式 】C46H70O9SSi2 【 分 子 量 】855.2934 【元素组成】C 64.6% H 8.25% O 16.84% S 3.75% Si 6.57% |
合成路线1
该中间体在本合成路线中的序号：(XLVI)Iodomethyl tetrahydropyran intermediate (XLVII): The condensation between epoxides (XLII), (XLIV) and silylated 1,3-dithiane (XLIII) gives the dihydroxy compound (XLV), which is treated first with 2,2-dimethoxypropane (XVIII) to create an acetonide group, and then with Hg(ClO4)2 to promote cyclization to yield the tetrahydropyran derivative (XLVI). Finally, the TsO group of (XLVI) is treated with lithium iodide in methanol to afford the desired iodomethyl tetrahydropyran intermediate (XLVII)
| 【1】 Smith, A.B.; et al.; The spongistatins: Architecturally complex natural products - Part one: A formal synthesis of (+)-spongistatin 1 by construction of an advanced ABCD fragment. Angew Chem. Int Ed 2001, 40, 1, 191. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XVIII) | 10722 | 1-Methoxy-1-methylethyl methyl ether; 2,2-Dimethoxypropane | 77-76-9 | C5H12O2 | 详情 | 详情 |
| (XLII) | 64630 | tert-butyl(diphenyl)silyl (3S)-4-[(2S)oxiranyl]-3-[(triethylsilyl)oxy]butyl ether; (7S)-9,9-diethyl-2,2-dimethyl-7-[(2S)oxiranylmethyl]-3,3-diphenyl-4,8-dioxa-3,9-disilaundecane | C28H44O3Si2 | 详情 | 详情 | |
| (XLIII) | 64631 | tert-butyl(1,3-dithian-2-yl)dimethylsilane | C10H22S2Si | 详情 | 详情 | |
| (XLIV) | 64632 | (4R)-2,2-dimethyl-4-{[(2S)-2-methyloxiranyl]methyl}-1,3-dioxolane | C9H16O3 | 详情 | 详情 | |
| (XLV) | 64633 | (2R,4S)-4-{[tert-butyl(dimethyl)silyl]oxy}-5-[2-((2S,4S)-6-{[tert-butyl(diphenyl)silyl]oxy}-2,4-dihydroxyhexyl)-1,3-dithian-2-yl]-2,4-dimethylpentyl 4-methylbenzenesulfonate | C46H72O7S3Si2 | 详情 | 详情 | |
| (XLVI) | 64634 | ((2R,4S,6R)-4-{[tert-butyl(dimethyl)silyl]oxy}-6-{[(4S,6S)-6-(2-{[tert-butyl(diphenyl)silyl]oxy}ethyl)-2,2-dimethyl-1,3-dioxan-4-yl]methyl}-6-methoxy-4-methyltetrahydro-2H-pyran-2-yl)methyl 4-methylbenzenesulfonate | C46H70O9SSi2 | 详情 | 详情 | |
| (XLVII) | 64635 | tert-butyl(dimethyl)silyl (2R,4S,6R)-2-{[(4S,6S)-6-(2-{[tert-butyl(diphenyl)silyl]oxy}ethyl)-2,2-dimethyl-1,3-dioxan-4-yl]methyl}-6-(iodomethyl)-2-methoxy-4-methyltetrahydro-2H-pyran-4-yl ether; tert-butyl[2-((4S,6S)-6-{[(2R,4S,6R)-4-{[tert-butyl(dimethyl)silyl]oxy}-6-(iodomethyl)-2-methoxy-4-methyltetrahydro-2H-pyran-2-yl]methyl}-2,2-dimethyl-1,3-dioxan-4-yl)ethoxy]diphenylsilane | C39H63IO6Si2 | 详情 | 详情 |