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【结 构 式】

【分子编号】31751

【品名】ethyl (E,4S,5S)-5-[(tert-butoxycarbonyl)amino]-4-(dibenzylamino)-5-phenyl-2-pentenoate

【CA登记号】

【 分 子 式 】C32H38N2O4

【 分 子 量 】514.6648

【元素组成】C 74.68% H 7.44% N 5.44% O 12.43%

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:(VIII)

Swern oxidation of N,N-dibenzyl-O-(tert-butyldimethylsilyl)serinol (I) afforded the intermediate aldehyde (II), which was condensed with phenylmagnesium bromide to give carbinol (III) as the major diastereoisomer. Displacement of the hydroxyl group of (III) with diphenylphosphoryl azide in the presence of diethyl azodicarboxylate and triphenylphosphine provided azide (IV). This was reduced to the corresponding amine with concomitant desilylation using LiAlH4. Further in situ addition of (Boc)2O produced carbamate (V). The alcohol function of (V) was then oxidized under Swern conditions, and the resulting aldehyde (VI) was condensed with phosphonate (VII) to yield unsaturated ester (VIII). Reduction of (VIII) to the saturated ester (IX) with Mg in MeOH, and further reduction of the ester group employing lithium borohydride gave rise to alcohol (X). After conversion of (X) to mesylate (XI), cyclization in the presence of NaH in THF furnished piperidine (XII). Debenzylation of (XII) afforded primary amine (XIII), which was reductively alkylated with 2-methoxybenzaldehyde (XIV) in the presence of NaCNBH3 to provide (XV). Finally, acid deprotection of the Boc group of (XV) yielded the title compound.

1 Chandrasekhar, S.; Mohanty, P.K.; Stereoselective synthesis of (+)-CP-99,994: A substance P non-peptide antagonist. Tetrahedron Lett 1999, 40, 27, 5071.
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) 31745 (2R)-3-[[tert-butyl(dimethyl)silyl]oxy]-2-(dibenzylamino)-1-propanol C23H35NO2Si 详情 详情
(II) 31746 (2S)-3-[[tert-butyl(dimethyl)silyl]oxy]-2-(dibenzylamino)propanal C23H33NO2Si 详情 详情
(III) 31747 (1R,2S)-3-[[tert-butyl(dimethyl)silyl]oxy]-2-(dibenzylamino)-1-phenyl-1-propanol C29H39NO2Si 详情 详情
(IV) 31748 N-[(1R,2S)-2-azido-1-([[tert-butyl(dimethyl)silyl]oxy]methyl)-2-phenylethyl]-N,N-dibenzylamine; (1S,2R)-1-azido-N,N-dibenzyl-3-[[tert-butyl(dimethyl)silyl]oxy]-1-phenyl-2-propanamine C29H38N4OSi 详情 详情
(V) 31749 tert-butyl (1S,2R)-2-(dibenzylamino)-3-hydroxy-1-phenylpropylcarbamate C28H34N2O3 详情 详情
(VI) 31750 tert-butyl (1S,2R)-2-(dibenzylamino)-3-oxo-1-phenylpropylcarbamate C28H32N2O3 详情 详情
(VII) 14182 ethyl 2-(triphenyl-lambda(5)-phosphanylidene)acetate; (Carbethoxymethylene)triphenylphosphorane 1099-45-2 C22H21O2P 详情 详情
(VIII) 31751 ethyl (E,4S,5S)-5-[(tert-butoxycarbonyl)amino]-4-(dibenzylamino)-5-phenyl-2-pentenoate C32H38N2O4 详情 详情
(IX) 31752 ethyl (4S,5S)-5-[(tert-butoxycarbonyl)amino]-4-(dibenzylamino)-5-phenylpentanoate C32H40N2O4 详情 详情
(X) 31753 tert-butyl (1S,2S)-2-(dibenzylamino)-5-hydroxy-1-phenylpentylcarbamate C30H38N2O3 详情 详情
(XI) 31754 (4S,5S)-5-[(tert-butoxycarbonyl)amino]-4-(dibenzylamino)-5-phenylpentyl methanesulfonate C31H40N2O5S 详情 详情
(XII) 31755 tert-butyl (2S,3S)-3-(dibenzylamino)-2-phenyl-1-piperidinecarboxylate C30H36N2O2 详情 详情
(XIII) 31756 tert-butyl (2S,3S)-3-amino-2-phenyl-1-piperidinecarboxylate C16H24N2O2 详情 详情
(XIV) 12568 2-Methoxybenzaldehyde; o-Methoxybenzaldehyde 135-02-4 C8H8O2 详情 详情
(XV) 31757 tert-butyl (2S,3S)-3-[(2-methoxybenzyl)amino]-2-phenyl-1-piperidinecarboxylate C24H32N2O3 详情 详情
Extended Information