(1S,2R,3S,4R,8R,9R)-4-benzyl-9-(benzyloxy)-2,3-dihydroxy-5-[(1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-indazol-5-yl)methyl]-5,7-diazatricyclo[6.2.2.0(1,7)]dodecan-6-one -Drug Synthesis Database

【结构式】

【分子编号】29594

【品名】(1S,2R,3S,4R,8R,9R)-4-benzyl-9-(benzyloxy)-2,3-dihydroxy-5-[(1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-indazol-5-yl)methyl]-5,7-diazatricyclo[6.2.2.0(1,7)]dodecan-6-one

【CA登记号】

【分子式】C₃₈H₄₈N₄O₅Si

【分子量】668.90858

【元素组成】C 68.23% H 7.23% N 8.38% O 11.96% Si 4.2%

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：(XV)

After N-alkylation of (X) with the protected bromomethylindazole (XI) to give (XII), acid hydrolysis of the acetonide yielded diol (XIII). In order to invert the undesired configuration at C4, the 4-hydroxyl group of (XIII) was selectively oxidized under Swern conditions to produce hydroxyketone (XIV). Subsequent reduction of (XIV) with ethanolic NaBH4 provided the required (4S,5R)-diol (XV). The silylethoxymethyl protecting group was finally removed with tetrabutylammonium fluoride in THF to afford the title compound.

参考文献中间体

合成目标

【1】 Han, W.; Pelletier, J.C.; Hodge, C.N.; Tricyclic ureas: A new class of HIV-1 protease inhibitors. Bioorg Med Chem Lett 1998, 8, 24, 3615.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(X)	29589	(1S,2R,6R,7R,11R,12R)-7-benzyl-12-(benzyloxy)-4,4-dimethyl-3,5-dioxa-8,10-diazatetracyclo[9.2.2.0(1,10).0(2,6)]pentadecan-9-one	C₂₇H₃₂N₂O₄	详情	详情
(XI)	29590	5-(bromomethyl)-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-indazole; [5-(bromomethyl)-1H-indazol-1-yl]methyl 2-(trimethylsilyl)ethyl ether	C₁₄H₂₁BrN₂OSi	详情	详情
(XII)	29591	(1S,2R,6R,7R,11R,12R)-7-benzyl-12-(benzyloxy)-4,4-dimethyl-8-[(1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-indazol-5-yl)methyl]-3,5-dioxa-8,10-diazatetracyclo[9.2.2.0(1,10).0(2,6)]pentadecan-9-one	C₄₁H₅₂N₄O₅Si	详情	详情
(XIII)	29592	(1S,2R,3R,4R,8R,9R)-4-benzyl-9-(benzyloxy)-2,3-dihydroxy-5-[(1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-indazol-5-yl)methyl]-5,7-diazatricyclo[6.2.2.0(1,7)]dodecan-6-one	C₃₈H₄₈N₄O₅Si	详情	详情
(XIV)	29593	(1S,2R,4R,8R,9R)-4-benzyl-9-(benzyloxy)-2-hydroxy-5-[(1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-indazol-5-yl)methyl]-5,7-diazatricyclo[6.2.2.0(1,7)]dodecane-3,6-dione	C₃₈H₄₆N₄O₅Si	详情	详情
(XV)	29594	(1S,2R,3S,4R,8R,9R)-4-benzyl-9-(benzyloxy)-2,3-dihydroxy-5-[(1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-indazol-5-yl)methyl]-5,7-diazatricyclo[6.2.2.0(1,7)]dodecan-6-one	C₃₈H₄₈N₄O₅Si	详情	详情

Extended Information