|
【结 构 式】 
|
【分子编号】42377 【品名】(4S,6R)-6-([[tert-butyl(dimethyl)silyl]oxy]methyl)-4-(iodomethyl)-4-methyl-1,3-dioxan-2-one 【CA登记号】 |
【 分 子 式 】C13H25IO4Si 【 分 子 量 】400.32907 【元素组成】C 39% H 6.29% I 31.7% O 15.99% Si 7.02% |
合成路线1
该中间体在本合成路线中的序号：(XI)Synthesis of intermediate (XIV): The condensation of epoxide (VIII) with isopropenyl bromide (IX) by means of n-BuLi and CuCN gives the alcohol (X), which is treated with 2-(tert-butoxycarbonyloxyimino)-2-phenylacetonitrile (Boc-ON) and n-BuLi in toluene to yield the cyclic carbonate (XI). The epoxidation of (XI) with HOAc in THF affords the epoxide (XII), which is selectively monoprotected with ethyl vinyl ether to provide the secondary alcohol (XIII). Finally this compound is silylated with TBDMSCl and imidazole to furnish the desired intermediate (XIV).
| 【1】 Guo, J.; et al.; Total synthesis of altohyrtin A (spongistatin 1): Part 1. Angew Chem. Int Ed Engl 1998, 37, 1-2, 187. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 18762 | 1-Ethoxyethylene; Ethyl vinyl ether；Ethoxyethene | 109-92-2 | C4H8O | 详情 | 详情 | |
| (VIII) | 42374 | tert-butyl(dimethyl)[(2R)oxiranylmethoxy]silane; tert-butyl(dimethyl)silyl (2R)oxiranylmethyl ether | C9H20O2Si | 详情 | 详情 | |
| (IX) | 42375 | 2-bromo-1-propene；2-bromopropene;Isopropenyl bromide;a-Methylvinyl bromide | 557-93-7 | C3H5Br | 详情 | 详情 |
| (X) | 42376 | (2R)-1-[[tert-butyl(dimethyl)silyl]oxy]-4-methyl-4-penten-2-ol | C12H26O2Si | 详情 | 详情 | |
| (XI) | 42377 | (4S,6R)-6-([[tert-butyl(dimethyl)silyl]oxy]methyl)-4-(iodomethyl)-4-methyl-1,3-dioxan-2-one | C13H25IO4Si | 详情 | 详情 | |
| (XII) | 42378 | (2R)-3-[(2S)-2-methyloxiranyl]-1,2-propanediol | C6H12O3 | 详情 | 详情 | |
| (XIII) | 42379 | (2R)-1-(2-ethoxyethoxy)-3-[(2S)-2-methyloxiranyl]-2-propanol | C10H20O4 | 详情 | 详情 | |
| (XIV) | 42380 | tert-butyl(dimethyl)silyl (1R)-2-(2-ethoxyethoxy)-1-[[(2S)-2-methyloxiranyl]methyl]ethyl ether; (5R)-2,2,3,3-tetramethyl-5-[[(2S)-2-methyloxiranyl]methyl]-4,7,10-trioxa-3-siladodecane | C16H34O4Si | 详情 | 详情 |