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【结 构 式】 
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【分子编号】46059 【品名】(6S)-3-bromo-2,2,6-trimethyl-6-vinyltetrahydro-2H-pyran 【CA登记号】 |
【 分 子 式 】C10H17BrO 【 分 子 量 】233.14838 【元素组成】C 51.52% H 7.35% Br 34.27% O 6.86% |
合成路线1
该中间体在本合成路线中的序号：(III)The reaction of (S)-linalool (I) with 2,4,4,6-tetrabromocyclohexa-2,5-dienone (TBCO) in nitromethane gives a mixture of tetrahydrofuran (II) and tetrahydropyran (III), which are separated by chromatography. The vinyl group of (III) is oxidized with OsO4 and NaIO4, yielding a diastereomeric mixture of aldehydes that is separated by chromatography to afford the target aldehydic intermediate (IV).
| 【1】 Forsyth, G.J.; Gonzalez, I.C.; Total synthesis of tryrsiferyl 23-acetate, a specific inhibitor of protein phosphatase 2A and anti-leukemic inducer of apoptosis. J Am Chem Soc 2000, 122, 38, 9099. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 46057 | (3S)-3,7-dimethyl-1,6-octadien-3-ol | C10H18O | 详情 | 详情 | |
| (II) | 46058 | (2S)-5-(1-bromo-1-methylethyl)-2-methyl-2-vinyltetrahydrofuran | C10H17BrO | 详情 | 详情 | |
| (III) | 46059 | (6S)-3-bromo-2,2,6-trimethyl-6-vinyltetrahydro-2H-pyran | C10H17BrO | 详情 | 详情 | |
| (IV) | 46060 | (2S,5R)-5-bromo-2,6,6-trimethyltetrahydro-2H-pyran-2-carbaldehyde | C9H15BrO2 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(III)The reaction of (S)-linalool (I) with 2,4,4,6-tetrabromocyclohexa-2,5-dienone (TBCO) in nitromethane gives a mixture of tetrahydrofuran (II) and tetrahydropyran (III), which are separated by chromatography. The vinyl group of (III) is oxidized with OsO4 and NaIO4, yielding a diastereomeric mixture of aldehydes that is separated by chromatography to afford the target aldehydic intermediate (IV).
| 【1】 Forsyth, G.J.; Gonzalez, I.C.; Total synthesis of tryrsiferyl 23-acetate, a specific inhibitor of protein phosphatase 2A and anti-leukemic inducer of apoptosis. J Am Chem Soc 2000, 122, 38, 9099. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 46057 | (3S)-3,7-dimethyl-1,6-octadien-3-ol | C10H18O | 详情 | 详情 | |
| (II) | 46058 | (2S)-5-(1-bromo-1-methylethyl)-2-methyl-2-vinyltetrahydrofuran | C10H17BrO | 详情 | 详情 | |
| (III) | 46059 | (6S)-3-bromo-2,2,6-trimethyl-6-vinyltetrahydro-2H-pyran | C10H17BrO | 详情 | 详情 | |
| (IV) | 46060 | (2S,5R)-5-bromo-2,6,6-trimethyltetrahydro-2H-pyran-2-carbaldehyde | C9H15BrO2 | 详情 | 详情 |
合成路线3
该中间体在本合成路线中的序号：(III)The reaction of (S)-linalool (I) with 2,4,4,6-tetrabromocyclohexa-2,5-dienone (TBCO) in nitromethane gives a mixture of tetrahydrofuran (II) and tetrahydropyran (III), which are separated by chromatography. The vinyl group of (III) is oxidized with OsO4 and NaIO4, yielding a diastereomeric mixture of aldehydes that is separated by chromatography to afford the target aldehydic intermediate (IV).
| 【1】 Forsyth, G.J.; Gonzalez, I.C.; Total synthesis of tryrsiferyl 23-acetate, a specific inhibitor of protein phosphatase 2A and anti-leukemic inducer of apoptosis. J Am Chem Soc 2000, 122, 38, 9099. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 46057 | (3S)-3,7-dimethyl-1,6-octadien-3-ol | C10H18O | 详情 | 详情 | |
| (II) | 46058 | (2S)-5-(1-bromo-1-methylethyl)-2-methyl-2-vinyltetrahydrofuran | C10H17BrO | 详情 | 详情 | |
| (III) | 46059 | (6S)-3-bromo-2,2,6-trimethyl-6-vinyltetrahydro-2H-pyran | C10H17BrO | 详情 | 详情 | |
| (IV) | 46060 | (2S,5R)-5-bromo-2,6,6-trimethyltetrahydro-2H-pyran-2-carbaldehyde | C9H15BrO2 | 详情 | 详情 |