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【结 构 式】

【分子编号】53243

【品名】(3S)-3-(2-bromoethoxy)-4-[(triisopropylsilyl)oxy]-1-butanol

【CA登记号】n/a

【 分 子 式 】C15H33BrO3Si

【 分 子 量 】369.41472

【元素组成】C 48.77% H 9% Br 21.63% O 12.99% Si 7.6%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(V)

A new synthesis of (9S)-9-(hydroxymethyl)-6,7,10,11- tetrahydro-9H,18H-5,21:12,17-dimethenodibenzo[e,k]pyrrolo[3,4-h][1,4,13]oxadiazacyclohexadecine-18,20-dione (XI), a key intermediate in the synthesis of LY-333531, has been reported: Enantiocontrolled condensation of 2-bromoethanol (I) with epoxide (II) by means of a chiral Pd catalyst, triethylborane and DMAP in dichloromethane gives the chiral allyl ether (III), which is protected with TIPS-OTf yielding the silyl ether (IV). Hydroboration of ether (IV) with 9-BBN followed by oxidation with H2O2 provides the primary alcohol (V), which is mesylated with MsCl to afford the mesylate (VI). Mesylate (VI) is cyclized with the bisindolylmaleimide (VII) by means of Cs2CO3 in DMF at 100 C resulting in the macrocyclic compound (VIII). Hydrolysis of (VIII) with KOH, followed by acidic workup yields the anhydride (IX), which by treatment with HMDS in methanolic DMF provides the maleimide (X). Finally, this compound is desilyl-ated with TBAF to afford the target intermediate (XI).

1 Trost, B.M.; Tang, W.; An enantioselective strategy to macrocyclic bisinsolylmaleimides, an efficient formal synthesis of LY 333531. Org Lett 2001, 3, 21, 3409.
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) 10059 Ethylene bromohydrin; 2-Bromo-1-ethanol 540-51-2 C2H5BrO 详情 详情
(II) 32805 2-vinyloxirane 930-22-3 C4H6O 详情 详情
(III) 53241 (2S)-2-(2-bromoethoxy)-3-buten-1-ol n/a C6H11BrO2 详情 详情
(IV) 53242 {[(2S)-2-(2-bromoethoxy)-3-butenyl]oxy}(triisopropyl)silane; (2S)-2-(2-bromoethoxy)-3-butenyl triisopropylsilyl ether n/a C15H31BrO2Si 详情 详情
(V) 53243 (3S)-3-(2-bromoethoxy)-4-[(triisopropylsilyl)oxy]-1-butanol n/a C15H33BrO3Si 详情 详情
(VI) 53244 (3S)-3-(2-bromoethoxy)-4-[(triisopropylsilyl)oxy]butyl methanesulfonate n/a C16H35BrO5SSi 详情 详情
(VII) 53245 1-benzyl-3,4-di(1H-indol-3-yl)-1H-pyrrole-2,5-dione n/a C27H19N3O2 详情 详情
(VIII) 53246 (18S)-4-benzyl-18-{[(triisopropylsilyl)oxy]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 n/a C42H49N3O4Si 详情 详情
(IX) 53247 (18S)-18-{[(triisopropylsilyl)oxy]methyl}-4,17-dioxa-14,21-diazahexacyclo[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 n/a C35H42N2O5Si 详情 详情
(X) 53248 (18S)-18-{[(triisopropylsilyl)oxy]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 n/a C35H43N3O4Si 详情 详情
(XI) 41013 (18S)-18-(hydroxymethyl)-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 C26H23N3O4 详情 详情
Extended Information