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【结 构 式】

【分子编号】47848

【品名】tert-butyl (3S)-3-[[tert-butyl(dimethyl)silyl]oxy]-2-[2-hydroxy-3-[4-oxo-3(4H)-quinazolinyl]propyl]-1-piperidinecarboxylate

【CA登记号】

【 分 子 式 】C27H43N3O5Si

【 分 子 量 】517.74114

【元素组成】C 62.64% H 8.37% N 8.12% O 15.45% Si 5.42%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(XXI)

After protection of (XVI) as the N-Boc derivative (XVII), the diol function was cyclized to epoxide (XIX) by treatment with N-tosyl imidazole (XVIII) in the presence of NaH. Epoxide (XIX) opening with the potassium salt of 4-quinazolinone (XX) gave alcohol (XXI). Subsequent Dess-Martin oxidation of (XXI) yielded the epimeric mixture of ketones (XXII). Acid hydrolysis of this mixture furnished the title trans-piperidine along with the cis-isomer, which was isolated in the cyclic hemiacetal form (XXIII). The title compound was also obtained by isomerization of (XXIII) in refluxing MeOH).

1 Ooi, H.e; et al.; A concise enantioselective synthesis of antimalarial febrifugine alkaloids. Org Lett 2001, 3, 6, 953.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XVI) 47844 3-((3S)-3-[[tert-butyl(diphenyl)silyl]oxy]piperidinyl)-1,2-propanediol C24H35NO3Si 详情 详情
(XVII) 47845 tert-butyl (3S)-3-[[tert-butyl(dimethyl)silyl]oxy]-2-(2,3-dihydroxypropyl)-1-piperidinecarboxylate C19H39NO5Si 详情 详情
(XVIII) 47846 1-[(4-methylphenyl)sulfonyl]-1H-imidazole 2232-08-8 C10H10N2O2S 详情 详情
(XIX) 47847 tert-butyl (3S)-3-[[tert-butyl(dimethyl)silyl]oxy]-2-(2-oxiranylmethyl)-1-piperidinecarboxylate C19H37NO4Si 详情 详情
(XX) 14634 4(3H)-quinazolinone C8H6N2O 详情 详情
(XXI) 47848 tert-butyl (3S)-3-[[tert-butyl(dimethyl)silyl]oxy]-2-[2-hydroxy-3-[4-oxo-3(4H)-quinazolinyl]propyl]-1-piperidinecarboxylate C27H43N3O5Si 详情 详情
(XXII) 47849 tert-butyl (3S)-3-[[tert-butyl(dimethyl)silyl]oxy]-2-[2-oxo-3-[4-oxo-3(4H)-quinazolinyl]propyl]-1-piperidinecarboxylate C27H41N3O5Si 详情 详情
(XXIII) 38272 3-[[(3aS,7aS)-2-hydroxyoctahydrofuro[3,2-b]pyridin-2-yl]methyl]-4(3H)-quinazolinone C16H19N3O3 详情 详情

合成路线2

该中间体在本合成路线中的序号:(XXI)

After protection of (XVI) as the N-Boc derivative (XVII), the diol function was cyclized to epoxide (XIX) by treatment with N-tosyl imidazole (XVIII) in the presence of NaH. Epoxide (XIX) opening with the potassium salt of 4-quinazolinone (XX) gave alcohol (XXI). Subsequent Dess-Martin oxidation of (XXI) yielded the epimeric mixture of ketones (XXII). Acid hydrolysis of this mixture furnished the trans-piperidine (XXIII) along with the title cis-isomer, which was isolated in the cyclic hemiacetal form.

1 Ooi, H.e; et al.; A concise enantioselective synthesis of antimalarial febrifugine alkaloids. Org Lett 2001, 3, 6, 953.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XVI) 47844 3-((3S)-3-[[tert-butyl(diphenyl)silyl]oxy]piperidinyl)-1,2-propanediol C24H35NO3Si 详情 详情
(XVII) 47845 tert-butyl (3S)-3-[[tert-butyl(dimethyl)silyl]oxy]-2-(2,3-dihydroxypropyl)-1-piperidinecarboxylate C19H39NO5Si 详情 详情
(XVIII) 47846 1-[(4-methylphenyl)sulfonyl]-1H-imidazole 2232-08-8 C10H10N2O2S 详情 详情
(XIX) 47847 tert-butyl (3S)-3-[[tert-butyl(dimethyl)silyl]oxy]-2-(2-oxiranylmethyl)-1-piperidinecarboxylate C19H37NO4Si 详情 详情
(XX) 14634 4(3H)-quinazolinone C8H6N2O 详情 详情
(XXI) 47848 tert-butyl (3S)-3-[[tert-butyl(dimethyl)silyl]oxy]-2-[2-hydroxy-3-[4-oxo-3(4H)-quinazolinyl]propyl]-1-piperidinecarboxylate C27H43N3O5Si 详情 详情
(XXII) 47849 tert-butyl (3S)-3-[[tert-butyl(dimethyl)silyl]oxy]-2-[2-oxo-3-[4-oxo-3(4H)-quinazolinyl]propyl]-1-piperidinecarboxylate C27H41N3O5Si 详情 详情
(XXIII) 47850 3-[3-[(2R,3S)-3-hydroxypiperidinyl]-2-oxopropyl]-4(3H)-quinazolinone C16H19N3O3 详情 详情
Extended Information