|
【结 构 式】 
|
【分子编号】51948 【品名】(7S)-2,11,11-trimethyl-7-(2-[[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]ethyl)-2-methylene-10,10-diphenyl-3,6,9-trioxa-2lambda(6)-thia-10-sila-1-dodecene; tert-butyl(diphenyl)silyl (2S)-4-[[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]-2-(2-[[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]ethoxy)butyl ether 【CA登记号】 |
【 分 子 式 】C28H44O4S2Si 【 分 子 量 】536.87246 【元素组成】C 62.64% H 8.26% O 11.92% S 11.95% Si 5.23% |
合成路线1
该中间体在本合成路线中的序号：(XXI)Alternatively, compound (XV) can also be obtained as follows: Reduction of (S)-maleate (XVI) with BMS-NaBH4 in THF, followed by O-protection with TBDPS-Cl and imidazole, yields alcohol (XVII), which is first allylated with allyl trichloroacetimidate (XVIII) catalyzed by triflic acid in cyclohexanes and then reduced with DIBAL in THF to provide compound (XIX). Ozonolysis of (XIX) in MeOH, followed by reductive quench with NaBH4, gives diol (XX), which is then converted into bismesylate (XXI) by treatment with MsCl and Et3N in ether. Compound (XXI) is subjected to a double Finkelstein reaction with NaI in acetone in the presence of NaHCO3 to yield bisiodide (XXII) (1), which is then coupled with 3-bis(1H-indol-3-yl)-N-methylmaleimide (XI) by means of Cs2CO3 in DMF to give intermediate (XV).
| 【1】 Engel, G.L.; Farid, N.A.; Faul, M.M.; Jirousek, M.R.; Richardson, L.A.; Winneroski, L.L. Jr. (Eli Lilly and Company); Protein kinase C inhibitor. EP 0776895; JP 1999500149; US 5710145; WO 9718809 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XI) | 41012 | 3,4-di(1H-indol-3-yl)-1-methyl-1H-pyrrole-2,5-dione | 113963-68-1 | C21H15N3O2 | 详情 | 详情 |
| (XV) | 41016 | (18S)-4-methyl-18-[(trityloxy)methyl]-17-oxa-4,14,21-triazahexacyclo[19.6.1.1(7,14).0(2,6).0(8,13).0(22,27)]nonacosa-1(28),2(6),7(29),8,10,12,22,24,26-nonaene-3,5-dione | C46H39N3O4 | 详情 | 详情 | |
| (XVI) | 11806 | dimethyl (2S)-2-hydroxybutanedioate | 617-55-0 | C6H10O5 | 详情 | 详情 |
| (XVII) | 41019 | methyl (3S)-4-[[tert-butyl(diphenyl)silyl]oxy]-3-hydroxybutanoate | C21H28O4Si | 详情 | 详情 | |
| (XVIII) | 51944 | N-(trichloromethyl)-3-butenamide | C5H6Cl3NO | 详情 | 详情 | |
| (XIX) | 41021 | (3S)-3-(allyloxy)-4-[[tert-butyl(diphenyl)silyl]oxy]-1-butanol | C23H32O3Si | 详情 | 详情 | |
| (XX) | 41023 | (3S)-4-[[tert-butyl(diphenyl)silyl]oxy]-3-(2-hydroxyethoxy)-1-butanol | C22H32O4Si | 详情 | 详情 | |
| (XXI) | 51948 | (7S)-2,11,11-trimethyl-7-(2-[[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]ethyl)-2-methylene-10,10-diphenyl-3,6,9-trioxa-2lambda(6)-thia-10-sila-1-dodecene; tert-butyl(diphenyl)silyl (2S)-4-[[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]-2-(2-[[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]ethoxy)butyl ether | C28H44O4S2Si | 详情 | 详情 | |
| (XXII) | 41025 | tert-butyl(diphenyl)silyl (2S)-4-iodo-2-(2-iodoethoxy)butyl ether; tert-butyl[[(2S)-4-iodo-2-(2-iodoethoxy)butyl]oxy]diphenylsilane | C22H30I2O2Si | 详情 | 详情 |