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【结 构 式】 
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【分子编号】20207 【品名】3-[13(R)-[5(R)-[5(R)-(1(S)-Acetoxyundecyl)tetrahydrofuran-2(R)-yl]tetrahydrofuran-2(R)-yl]-13-hydroxytridecyl]-5(S)-methyl-3-(phenylsulfanyl)tetrahydrofuran-2-one 【CA登记号】 |
【 分 子 式 】C45H74O7S 【 分 子 量 】759.14436 【元素组成】C 71.2% H 9.83% O 14.75% S 4.22% |
合成路线1
该中间体在本合成路线中的序号：(XXVI)3) The addition of the iodinated tetrahydofuranone (XXIV) to the triple bond of (XXIII) catalyzed by CuI and palladium tetrakis(triphenylphosphine) in triethylamine yields intermediate (XXV) with a double and a triple bonds that are hydrogenated with H2 over a rhodium triphenylphosphine complex in benzene/methanol affording the saturated tridecanol (XXVI). Finally, the double bond of the dihydrofuranone ring of uvaricin is formed by oxidation of the phenylsulfanyl group to the corresponding sulfonyl derivative with m-chloroperbenzoic acid in dichloromethane followed by elimination of benzenesulfonic acid by refluxing in toluene.
| 【1】 Yazbak, A.; et al.; Total synthesis of uvaricin. J Org Chem 1998, 63, 17, 5863. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XXIV) | 20205 | (5S)-3-[(E)-9-iodo-8-nonenyl]-5-methyl-3-(phenylsulfanyl)dihydro-2(3H)-furanone | C20H27IO2S | 详情 | 详情 | |
| (XXV) | 20206 | 3-[13(R)-[5(R)-[5(R)-(1(S)-Acetoxyundecyl)tetrahydrofuran-2(R)-yl]tetrahydrofuran-2(R)-yl]-13-hydroxytrideca-8(E)-en-10-ynyl]-5(S)-methyl-3-(phenylsulfanyl)tetrahydrofuran-2-one | C45H68O7S | 详情 | 详情 | |
| (XXVI) | 20207 | 3-[13(R)-[5(R)-[5(R)-(1(S)-Acetoxyundecyl)tetrahydrofuran-2(R)-yl]tetrahydrofuran-2(R)-yl]-13-hydroxytridecyl]-5(S)-methyl-3-(phenylsulfanyl)tetrahydrofuran-2-one | C45H74O7S | 详情 | 详情 |