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【结 构 式】 
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【分子编号】20204 【品名】(5S)-5-methyl-3-(phenylsulfanyl)dihydro-2(3H)-furanone 【CA登记号】 |
【 分 子 式 】C11H12O2S 【 分 子 量 】208.28108 【元素组成】C 63.43% H 5.81% O 15.36% S 15.4% |
合成路线1
该中间体在本合成路线中的序号：(XXXII)4) The intermediate iodinated tetrahydrofuranone (XXIV) has been obtained as follows: The silylation of 8-nonyn-1-ol (XXVII) with tert-butyldimethylsilyl chloride (TBDMS-Cl) and imidazole in DMF gives the silyl ether (XXVIII), which is iodinated by means of tributyltin hydride, azobis(cyclohexanecarbonitrile) (ABCN) and iodine yielding the iodovinyl compound (XXIX). The deprotection of (XXIX) with tetrabutylammonium fluoride in THF, followed by tosylation with tosyl chloride in pyridine affords the tosylate (XXX), which by reaction with NaI in acetone affords 1,9-diiodo-1-nonene (XXXI). Finally, this compound is condensed with (5S)-methyl-3-(phenylsulfanyl)tetrahydrofuran-2-one (XXXII) by means of potassium bis(trimthylsilyl)amide in THF to afford the desired intermediate (XXIV).
| 【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 | |
| (XXVII) | 20199 | 8-nonyn-1-ol | C9H16O | 详情 | 详情 | |
| (XXVIII) | 20200 | tert-butyl(dimethyl)(8-nonynyloxy)silane; tert-butyl(dimethyl)silyl 8-nonynyl ether | C15H30OSi | 详情 | 详情 | |
| (XXIX) | 20201 | tert-butyl[[(E)-9-iodo-8-nonenyl]oxy]dimethylsilane; tert-butyl(dimethyl)silyl (E)-9-iodo-8-nonenyl ether | C15H31IOSi | 详情 | 详情 | |
| (XXX) | 20202 | (E)-9-iodo-8-nonenyl 4-methylbenzenesulfonate | C16H23IO3S | 详情 | 详情 | |
| (XXXI) | 20203 | (E)-1,9-diiodo-1-nonene | C9H16I2 | 详情 | 详情 | |
| (XXXII) | 20204 | (5S)-5-methyl-3-(phenylsulfanyl)dihydro-2(3H)-furanone | C11H12O2S | 详情 | 详情 |