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【结 构 式】 
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【分子编号】62840 【品名】chloro[(E)-3-(trimethylsilyl)-2-propenyl]chromium 【CA登记号】 |
【 分 子 式 】C6H13ClCrSi 【 分 子 量 】200.70352 【元素组成】C 35.91% H 6.53% Cl 17.66% Cr 25.91% Si 13.99% |
合成路线1
该中间体在本合成路线中的序号：(XXI)Chiral octadienoic aldehyde intermediate (XXV): The reaction of the silylated allyl bromide (XX) with CrCl2 in THF gives the Cr derivative (XXI), which is condensed with the chiral pentanoic aldehyde intermediate (XIX) to yield the secondary alcohol (XXII). Elimination of the Tms group of (XXII) by means of KH in THF affords the desired (Z)-diene (XXIII), which is desilylated by means of CSA in methanol/dichloromethane to provide the primary alcohol (XXIV). Finally this compound is oxidized by means of DMP in dichloromethane to furnish the target, chiral octadienoic aldehyde intermediate (XXV).
| 【1】 Paterson, I.; Florence, G.J.; Gerlach, K.; Scott, J.P.; Sereinig, N.; A practical synthesis of (+)-discodermolide and analogues: Fragment union by complex aldol reactions. J Am Chem Soc 2001, 123, 39, 9535. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XIX) | 42628 | (2R,3R,4S)-5-[[tert-butyl(dimethyl)silyl]oxy]-3-[(4-methoxybenzyl)oxy]-2,4-dimethylpentanal | C21H36O4Si | 详情 | 详情 | |
| (XX) | 42629 | (1-bromo-2-propenyl)(trimethyl)silane | 94397-40-7 | C6H13BrSi | 详情 | 详情 |
| (XXI) | 62840 | chloro[(E)-3-(trimethylsilyl)-2-propenyl]chromium | C6H13ClCrSi | 详情 | 详情 | |
| (XXII) | 62841 | (3R,4S,5S,6R,7S)-8-{[tert-butyl(dimethyl)silyl]oxy}-6-[(4-methoxybenzyl)oxy]-5,7-dimethyl-3-(trimethylsilyl)-1-octen-4-ol | C27H50O4Si2 | 详情 | 详情 | |
| (XXIII) | 46630 | 2,4,4-trimethyl-5,6-dihydro-4H-1,3-oxazine | C7H13NO | 详情 | 详情 | |
| (XXIV) | 42631 | (2S,3S,4S,5Z)-3-[(4-methoxybenzyl)oxy]-2,4-dimethyl-5,7-octadien-1-ol | C18H26O3 | 详情 | 详情 | |
| (XXV) | 42632 | (2R,3S,4S,5Z)-3-[(4-methoxybenzyl)oxy]-2,4-dimethyl-5,7-octadienal | C18H24O3 | 详情 | 详情 |