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【结 构 式】 
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【分子编号】42457 【品名】triethyl[((1R,2S)-1-[2-[(4-methoxybenzyl)oxy]ethyl]-2-methyl-3-butenyl)oxy]silane; 4-methoxybenzyl (3R,4S)-4-methyl-3-[(triethylsilyl)oxy]-5-hexenyl ether 【CA登记号】 |
【 分 子 式 】C21H36O3Si 【 分 子 量 】364.60054 【元素组成】C 69.18% H 9.95% O 13.16% Si 7.7% |
合成路线1
该中间体在本合成路线中的序号：(X)Synthesis of alkyne (XIII). The reaction of the protected aldehyde (VIII) with (-)-(E)-crotyldiisopinocampheylborane (CDICB) by means of BF3/Et2O in THF gives the chiral unsaturated alcohol (IX), which is silylated with Tes-Cl and imidazole, yielding the protected unsaturated diol (X). Oxidation of the double bond of (X) with OsO4 and Pb(OAc)4 in toluene affords the aldehyde (XI), which is treated with CBr4, PPh3 and Et3N in dichloromethane to provide the dibromovinyl compound (XII). Finally, (XII) is treated with BuLi in THF to give the target acetylenic intermediate (XIII).
| 【1】 Shimizu, T.; et al.; Total synthesis of reveromycin A. Org Lett 2000, 2, 14, 2153. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (VIII) | 42455 | 3-[(4-methoxybenzyl)oxy]propanal | C11H14O3 | 详情 | 详情 | |
| (IX) | 42456 | (3R,4S)-1-[(4-methoxybenzyl)oxy]-4-methyl-5-hexen-3-ol | C15H22O3 | 详情 | 详情 | |
| (X) | 42457 | triethyl[((1R,2S)-1-[2-[(4-methoxybenzyl)oxy]ethyl]-2-methyl-3-butenyl)oxy]silane; 4-methoxybenzyl (3R,4S)-4-methyl-3-[(triethylsilyl)oxy]-5-hexenyl ether | C21H36O3Si | 详情 | 详情 | |
| (XI) | 42458 | (2R,3R)-5-[(4-methoxybenzyl)oxy]-2-methyl-3-[(triethylsilyl)oxy]pentanal | C20H34O4Si | 详情 | 详情 | |
| (XII) | 42459 | [((1R,2S)-4,4-dibromo-1-[2-[(4-methoxybenzyl)oxy]ethyl]-2-methyl-3-butenyl)oxy](triethyl)silane; (1R,2S)-4,4-dibromo-1-[2-[(4-methoxybenzyl)oxy]ethyl]-2-methyl-3-butenyl triethylsilyl ether | C21H34Br2O3Si | 详情 | 详情 | |
| (XIII) | 42460 | triethyl[((1R,2S)-1-[2-[(4-methoxybenzyl)oxy]ethyl]-2-methyl-3-butynyl)oxy]silane; 4-methoxybenzyl (3R,4S)-4-methyl-3-[(triethylsilyl)oxy]-5-hexynyl ether | C21H34O3Si | 详情 | 详情 |