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【结 构 式】 
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【分子编号】63106 【品名】(2S)-4-(phenylsulfonyl)-1-(tetrahydro-2H-pyran-2-yloxy)-2-butanol 【CA登记号】 |
【 分 子 式 】C15H22O5S 【 分 子 量 】314.40268 【元素组成】C 57.3% H 7.05% O 25.44% S 10.2% |
合成路线1
该中间体在本合成路线中的序号：(III)The intermediate carbaldehyde (VI) and Weinreb amide (IX) have been obtained as follows. The reaction of tetrahydropyranyl glycidol (I) with methyl phenylsulfone (II) by means of BuLi in THF gives the secondary alcohol (III), which is protected with Pmb-Cl and NaH in DMF to yield the diether (IV). Selective cleavage of the THP group of (IV) by means of CSA in methanol affords the primary alcohol (V), which is oxidized with (COCl)2 and DMSO in dichloromethane to provide the aldehyde (VI). Further oxidation of (VI) by means of NaClO2 in t-butanol gives the carboxylic acid (VII), which is finally condensed with N,O-dimethylhydroxylamine (VIII) by means of iso-butyl chloroformate in dichloromethane to yield the intermediate Weinreb amide (IX).
| 【1】 Ghosh, A.K.; Wang, Y.; Kim, J.T.; Total synthesis of microtubule-stabilizing agent (-)-laulimalide. J Org Chem 2001, 66, 26, 8973. |
| 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) | 63105 | 2-[(2R)oxiranyloxy]tetrahydro-2H-pyran; (2R)oxiranyl tetrahydro-2H-pyran-2-yl ether | C7H12O3 | 详情 | 详情 | |
| (II) | 23622 | methyl phenyl sulfone; methyl(dioxo)phenyl-lambda(6)-sulfane | 3112-85-4 | C7H8O2S | 详情 | 详情 |
| (III) | 63106 | (2S)-4-(phenylsulfonyl)-1-(tetrahydro-2H-pyran-2-yloxy)-2-butanol | C15H22O5S | 详情 | 详情 | |
| (IV) | 63107 | 2-{[(2S)-2-[(4-methoxybenzyl)oxy]-4-(phenylsulfonyl)butyl]oxy}tetrahydro-2H-pyran; (3S)-3-[(4-methoxybenzyl)oxy]-4-(tetrahydro-2H-pyran-2-yloxy)butyl phenyl sulfone | C23H30O6S | 详情 | 详情 | |
| (V) | 63108 | (2S)-2-[(4-methoxybenzyl)oxy]-4-(phenylsulfonyl)-1-butanol | C18H22O5S | 详情 | 详情 | |
| (VI) | 63109 | (2S)-2-[(4-methoxybenzyl)oxy]-4-(phenylsulfonyl)butanal | C18H20O5S | 详情 | 详情 | |
| (VII) | 63110 | (2S)-2-[(4-methoxybenzyl)oxy]-4-(phenylsulfonyl)butanoic acid | C18H20O6S | 详情 | 详情 | |
| (VIII) | 13361 | (Methoxyamino)methane; N,O-Dimethylhydroxylamine | 1117-97-1 | C2H7NO | 详情 | 详情 |
| (IX) | 63111 | (2S)-N-methoxy-2-[(4-methoxybenzyl)oxy]-N-methyl-4-(phenylsulfonyl)butanamide | C20H25NO6S | 详情 | 详情 |