methyl (4S,5R)-2,4-diphenyl-4,5-dihydro-1,3-oxazole-5-carboxylate -Drug Synthesis Database

【结构式】

【分子编号】61751

【品名】methyl (4S,5R)-2,4-diphenyl-4,5-dihydro-1,3-oxazole-5-carboxylate

【CA登记号】

【分子式】C₁₇H₁₅NO₃

【分子量】281.31104

【元素组成】C 72.58% H 5.37% N 4.98% O 17.06%

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：(III)

The cyclization of 2(R),3(S)-dihydroxy-3-phenylpropionic acid methyl ester (I) with benzonitrile (II) by means of conc. H2SO4 gives 2,4(S)-diphenyloxazolidine-5(S)-carboxylic acid methyl ester (III). Finally, this compound is submitted to an hydrolytic treatment with aq. H2SO4 to afford the target 3(S)-benzamido-2(R)-hydroxy-3-phenylpropionic acid (IV).

参考文献中间体

合成目标

【1】 Voronkov, M.V.; et al.; Improved large-scale synthesis of phenylisoserine and the taxol C-13 side chain. Tetrahedron Lett 2003, 44, 2, 407.

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)	23889	methyl (2S,3R)-2,3-dihydroxy-3-phenylpropanoate		C₁₀H₁₂O₄	详情	详情
(II)	25904	benzonitrile	100-47-0	C₇H₅N	详情	详情
(III)	61751	methyl (4S,5R)-2,4-diphenyl-4,5-dihydro-1,3-oxazole-5-carboxylate		C₁₇H₁₅NO₃	详情	详情
(IV)	31988	(2R,3S)-3-(benzoylamino)-2-hydroxy-3-phenylpropionic acid		C₁₆H₁₅NO₄	详情	详情

Extended Information