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【结 构 式】 
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【分子编号】57110 【品名】4,5,5-trimethyl-2-[2-(2-naphthyloxy)acetyl]-2-azabicyclo[2.2.1]heptan-3-one 【CA登记号】 |
【 分 子 式 】C21H23NO3 【 分 子 量 】337.41856 【元素组成】C 74.75% H 6.87% N 4.15% O 14.23% |
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：(I)The condensation of the chiral imide (I) with aldehyde (II) by means of Et2B-OTf and DIEA in dichloromethane gives the hydroxy-imide (III), which is protected with Tbdms-Cl and imidazole to yield the silyl ether (IV). The cleavage of the chiral auxiliary of (IV), followed by reduction with DIBAL in THF affords the aldehyde (V), which is condensed with the silylated enol ether (VI) by means of SnCl4 in dichloromethane to provide the target intermediate, the phenyl thioester (VII).
| 【1】 Boeckman, R.K.; Clark, T.J.; Shook, B.C.; A practical enantioselective total synthesis of the bengamides B, E, and Z. Org Lett 2002, 4, 12, 2109. |
| 【2】 Boeckman, R.K.; et al.; The development of a convergent and efficient enantioselective synthesis of the bengamides via a common polyol intermediate. Helv Chim Acta 2002, 85, 12, 4532. |
| 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) | 57110 | 4,5,5-trimethyl-2-[2-(2-naphthyloxy)acetyl]-2-azabicyclo[2.2.1]heptan-3-one | C21H23NO3 | 详情 | 详情 | |
| (II) | 57111 | 4-Methyl-2-pentenal | 5362-56-1 | C6H10O | 详情 | 详情 |
| (III) | 57112 | 2-[(2S,3R,4E)-3-hydroxy-6-methyl-2-(2-naphthyloxy)-4-heptenoyl]-4,5,5-trimethyl-2-azabicyclo[2.2.1]heptan-3-one | C27H33NO4 | 详情 | 详情 | |
| (IV) | 57113 | 2-[(2S,3R,4E)-3-{[tert-butyl(dimethyl)silyl]oxy}-6-methyl-2-(2-naphthyloxy)-4-heptenoyl]-4,5,5-trimethyl-2-azabicyclo[2.2.1]heptan-3-one | C33H47NO4Si | 详情 | 详情 | |
| (V) | 57114 | (2S,3R,4E)-3-{[tert-butyl(dimethyl)silyl]oxy}-6-methyl-2-(2-naphthyloxy)-4-heptenal | C24H34O3Si | 详情 | 详情 | |
| (VI) | 57115 | (Z)-2-methoxy-1-(phenylsulfanyl)ethenyl trimethylsilyl ether; {[(Z)-2-methoxy-1-(phenylsulfanyl)ethenyl]oxy}(trimethyl)silane | C12H18O2SSi | 详情 | 详情 | |
| (VII) | 57116 | S-phenyl (2R,3S,4R,5R,6E)-5-{[tert-butyl(dimethyl)silyl]oxy}-3-hydroxy-2-methoxy-8-methyl-4-(2-naphthyloxy)-6-nonenethioate | C33H44O5SSi | 详情 | 详情 |
Extended Information