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【结 构 式】 
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【分子编号】52064 【品名】tert-butyl[4-[(2S)oxiranylmethoxy]phenoxy]diphenylsilane; tert-butyl(diphenyl)silyl 4-[(2S)oxiranylmethoxy]phenyl ether 【CA登记号】 |
【 分 子 式 】C25H28O3Si 【 分 子 量 】404.58102 【元素组成】C 74.22% H 6.98% O 11.86% Si 6.94% |
合成路线1
该中间体在本合成路线中的序号：(V)4-Benzyloxyphenol (I) was protected as the silyl ether (II) upon treatment with tert-butyldiphenylsilyl chloride and imidazole. Then, benzyl ether cleavage in (II) by means of transfer hydrogenolysis with cyclohexene and Pd/C furnished the silyloxy phenol (III). Coupling of phenol (III) with (R)-glycidol (IV) under Mitsunobu conditions yielded the intermediate glycidyl ether (V).
| 【1】 Solvibile, W.R.; et al.; Potent, selective agonists of the human beta3-adrenergic receptor. 222nd ACS Natl Meet (Aug 26 2001, Chicago) 2001, Abst MEDI 35. |
| 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) | 18956 | 4-(Benzyloxy)phenol; 4-Benzyloxyphenol | 103-16-2 | C13H12O2 | 详情 | 详情 |
| (II) | 52062 | [4-(benzyloxy)phenoxy](tert-butyl)diphenylsilane; benzyl 4-[[tert-butyl(diphenyl)silyl]oxy]phenyl ether | C29H30O2Si | 详情 | 详情 | |
| (III) | 52063 | 4-[[tert-butyl(diphenyl)silyl]oxy]phenol | C22H24O2Si | 详情 | 详情 | |
| (IV) | 16260 | (R)-(+)-Glycidol; (2R)-Oxiranemethanol; (2R)oxiranylmethanol | 57044-25-4 | C3H6O2 | 详情 | 详情 |
| (V) | 52064 | tert-butyl[4-[(2S)oxiranylmethoxy]phenoxy]diphenylsilane; tert-butyl(diphenyl)silyl 4-[(2S)oxiranylmethoxy]phenyl ether | C25H28O3Si | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(V)The aliphatic amino group of 4-aminophenethylamine (VI) was regioselectively protected as the N-Boc derivative (VII) using Boc2O. Subsequent reductive alkylation of aniline (VII) with N-benzyl-4-piperidone (VIII) afforded the anilinopiperidine (IX). The N-benzyl group of (IX) was then removed by transfer hydrogenolysis, and the resulting piperidine (X) was condensed with octyl isocyanate (XI), yielding the corresponding urea (XII). After acidic cleavage of the N-Boc protecting group of (XII), the primary amine (XIII) was condensed with the intermediate epoxide (V) to produce the amino alcohol (XIV). Final desilylation of (XIV) gave rise to the title compound.
| 【1】 Solvibile, W.R.; et al.; Potent, selective agonists of the human beta3-adrenergic receptor. 222nd ACS Natl Meet (Aug 26 2001, Chicago) 2001, Abst MEDI 35. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (V) | 52064 | tert-butyl[4-[(2S)oxiranylmethoxy]phenoxy]diphenylsilane; tert-butyl(diphenyl)silyl 4-[(2S)oxiranylmethoxy]phenyl ether | C25H28O3Si | 详情 | 详情 | |
| (VI) | 18961 | 4-(2-aminoethyl)aniline; 4-(2-aminoethyl)phenylamine | 13472-00-9 | C8H12N2 | 详情 | 详情 |
| (VII) | 18966 | tert-butyl 4-aminophenethylcarbamate | C13H20N2O2 | 详情 | 详情 | |
| (VIII) | 15720 | 1-benzyltetrahydro-4(1H)-pyridinone; 1-Benzyl-4-piperidone; N-Benzyl-4-piperidone; 1-(benzyl)-4-piperidinone; 1-benzylpiperidin-4-one; 1-(benzyl)piperidin-4-one | 3612-20-2 | C12H15NO | 详情 | 详情 |
| (IX) | 52065 | tert-butyl 4-[(1-benzyl-4-piperidinyl)amino]phenethylcarbamate | C25H35N3O2 | 详情 | 详情 | |
| (X) | 52066 | tert-butyl 4-(4-piperidinylamino)phenethylcarbamate | C18H29N3O2 | 详情 | 详情 | |
| (XI) | 52067 | 1-isocyanatooctane; octyl isocyanate | C9H17NO | 详情 | 详情 | |
| (XII) | 52068 | tert-butyl 4-([1-[(octylamino)carbonyl]-4-piperidinyl]amino)phenethylcarbamate | C27H46N4O3 | 详情 | 详情 | |
| (XIII) | 52069 | 4-[4-(2-aminoethyl)anilino]-N-octyl-1-piperidinecarboxamide | C22H38N4O | 详情 | 详情 | |
| (XIV) | 52070 | 4-[4-(2-[[(2S)-3-(4-[[tert-butyl(diphenyl)silyl]oxy]phenoxy)-2-hydroxypropyl]amino]ethyl)anilino]-N-octyl-1-piperidinecarboxamide | C47H66N4O4Si | 详情 | 详情 |