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【结 构 式】 
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【分子编号】69039 【品名】(4R)-4-propyl-1,3,2-dioxathiolane 2-oxide 【CA登记号】 |
【 分 子 式 】C5H10O3S 【 分 子 量 】150.199 【元素组成】C 39.98% H 6.71% O 31.96% S 21.35% |
合成路线1
该中间体在本合成路线中的序号：(XVI)The Meldrum’s acid derivative (II) is prepared by the following method. Sharpless asymmetric dihydroxylation of 1-pentene (XIV) by means of AD-mix-β in tert-butanol/water produces (R)-1,2-pentanediol (XV), which is treated with SOCl2 in chloroform to generate the cyclic sulfite (XVI). This compound, without isolation, is oxidized with RuCl3 and NaIO4 to afford the cyclic sulfate (XVII), which is then condensed with dimethyl malonate (XVIII) by means of NaH in dimethoxyethane to provide the spirocyclopropane (XIX). Hydrolysis of the ester groups of (XIX) by means of aqueous NaOH gives the corresponding diacid (XX), which is reacted with acetone in the presence of H2SO4 to yield the target dioxane dione (II) .
| 【1】 Ates, C., Schule, A. (UCB SA). 3-Carboxy-2-oxo-1-pyrrolidine derivatives and their uses. EP 1993998, JP 2009518335, US 2009012313, WO 2007065634. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (II) | 69027 | (R)-6,6-dimethyl-1-propyl-5,7-dioxaspiro[2.5]octane-4,8-dione | C11H16O4 | 详情 | 详情 | |
| (XIV) | 69037 | 1-pentene;pent-1-ene;1-Methyl-3-butene;Propylethylene;a-n-Amylene | 109-67-1 | C5H10 | 详情 | 详情 |
| (XV) | 69038 | (R)-1,2-pentanediol；(R)-Pentane-1,2-diol；(2R)-1,2-Pentanediol | 108340-61-0 | C5H12O2 | 详情 | 详情 |
| (XVI) | 69039 | (4R)-4-propyl-1,3,2-dioxathiolane 2-oxide | C5H10O3S | 详情 | 详情 | |
| (XVII) | 69040 | (R)-4-propyl-1,3,2-dioxathiolane 2,2-dioxide | C5H10O4S | 详情 | 详情 | |
| (XVIII) | 19373 | dimethyl malonate；Methyl malonate;Propanedioic acid dimethyl ester | 108-59-8 | C5H8O4 | 详情 | 详情 |
| (XIX) | 69041 | (R)-dimethyl 2-propylcyclopropane-1,1-dicarboxylate | C10H16O4 | 详情 | 详情 | |
| (XX) | 69042 | (R)-2-propylcyclopropane-1,1-dicarboxylic acid | C8H12O4 | 详情 | 详情 |