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【结 构 式】

【分子编号】48361

【品名】methyl (4S,5S)-2-[(1R)-1-[(tert-butoxycarbonyl)amino]ethyl]-5-methyl-4,5-dihydro-1,3-oxazole-4-carboxylate

【CA登记号】

【 分 子 式 】C13H22N2O5

【 分 子 量 】286.32816

【元素组成】C 54.53% H 7.74% N 9.78% O 27.94%

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:(IVb)

The heterocyclic amino acid precursor (VI) was synthesized as follows. Coupling between N-Boc-D-alanine (I) and L-threonine methyl ester (II) in the presence of DCC and HOBt gave dipeptide (III). Cyclization of (III) using Burgess reagent provided the oxazoline (IV) as a mixture of diastereoisomers. Subsequent dehydrogenation of (IV) by means of bromotrichloromethane and DBU afforded the protected oxazole amino acid (V). Basic hydrolysis of the ethyl ester group then yielded the intermediate acid (VI).

1 Xia, Z.; Smith, C.D.; Total synthesis of dendroamide A, a novel cyclic peptide that reverses multiple drug resistance. J Org Chem 2001, 66, 10, 3459.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(IVa) 48360 methyl (4S,5R)-2-[(1R)-1-[(tert-butoxycarbonyl)amino]ethyl]-5-methyl-4,5-dihydro-1,3-oxazole-4-carboxylate C13H22N2O5 详情 详情
(IVb) 48361 methyl (4S,5S)-2-[(1R)-1-[(tert-butoxycarbonyl)amino]ethyl]-5-methyl-4,5-dihydro-1,3-oxazole-4-carboxylate C13H22N2O5 详情 详情
(I) 15859 Boc-D-Alanine; (2R)-2-[(tert-butoxycarbonyl)amino]propionic acid 7764-95-6 C8H15NO4 详情 详情
(II) 42026 methyl (2S,3R)-2-amino-3-hydroxybutanoate C5H11NO3 详情 详情
(III) 48359 methyl (2S,3R)-2-([(2R)-2-[(tert-butoxycarbonyl)amino]propanoyl]amino)-3-hydroxybutanoate C13H24N2O6 详情 详情
(V) 48362 methyl 2-[(1R)-1-[(tert-butoxycarbonyl)amino]ethyl]-5-methyl-1,3-oxazole-4-carboxylate C13H20N2O5 详情 详情
(VI) 48363 2-[(1R)-1-[(tert-butoxycarbonyl)amino]ethyl]-5-methyl-1,3-oxazole-4-carboxylic acid C12H18N2O5 详情 详情
Extended Information