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【结 构 式】 
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【分子编号】42382 【品名】(3R,4S,5R)-4,6-bis[[tert-butyl(dimethyl)silyl]oxy]-3,5-dimethylhexanal 【CA登记号】 |
【 分 子 式 】C20H44O3Si2 【 分 子 量 】388.73856 【元素组成】C 61.79% H 11.41% O 12.35% Si 14.45% |
与该中间体有关的原料药合成路线共 1 条
合成路线1
该中间体在本合成路线中的序号：(XVI)Synthesis of intermediate (XX): The oxidation of silylated diol (XV) with OsO4, Pb(OAc)4 and N-methylmorpholine-N-oxide (NMO) in acetone/benzene gives the aldehyde (XVI), which is condensed with formaldehyde by means of KOtBu and B-iodo-9-borabicyclo[3.3.1]nonane (B-I-9-BBN) to yield the iodovinyl compound (XVII). The desilylation of (XVII) with HF and pyridine in THF affords the diol (XVIII), which is treated with 1,1-dimethoxycyclohexane (XIX) and pyridinium p-toluenesulfonate (PPTS) to provide the desired intermediate (XX).
| 【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 |
|---|---|---|---|---|---|---|
| (XV) | 42381 | (5S,6R)-2,2,3,3,6,9,9,10,10-nonamethyl-5-[(1R)-1-methyl-2-propenyl]-4,8-dioxa-3,9-disilaundecane; tert-butyl(dimethyl)silyl (2R,3S,4R)-3-[[tert-butyl(dimethyl)silyl]oxy]-2,4-dimethyl-5-hexenyl ether | C20H44O2Si2 | 详情 | 详情 | |
| (XVI) | 42382 | (3R,4S,5R)-4,6-bis[[tert-butyl(dimethyl)silyl]oxy]-3,5-dimethylhexanal | C20H44O3Si2 | 详情 | 详情 | |
| (XVII) | 42383 | tert-butyl(dimethyl)silyl (2R,3R,4S)-3-[[tert-butyl(dimethyl)silyl]oxy]-5-iodo-2,4-dimethyl-5-hexenyl ether; (5R,6R)-5-[(1S)-2-iodo-1-methyl-2-propenyl]-2,2,3,3,6,9,9,10,10-nonamethyl-4,8-dioxa-3,9-disilaundecane | C20H43IO2Si2 | 详情 | 详情 | |
| (XVIII) | 42384 | (2R,3R,4S)-5-iodo-2,4-dimethyl-5-hexene-1,3-diol | C8H15IO2 | 详情 | 详情 | |
| (XIX) | 42385 | 1,1-dimethoxycyclohexane; 1-methoxycyclohexyl methyl ether | 933-40-4 | C8H16O2 | 详情 | 详情 |
| (XX) | 42386 | (2R,3R)-2-[(1S)-2-iodo-1-methyl-2-propenyl]-3-methyl-1,5-dioxaspiro[5.5]undecane | C14H23IO2 | 详情 | 详情 |
Extended Information