CAS: 198493-85-5; (2R,3R)-2-((Tert-Butoxycarbonyl)Amino)-3-Phenylbutanoic Acid

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90731-57-0 321524-48-5 115132-19-9

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methyl (2R,3R)-2-[(tert-butoxycarbonyl)amino]-3-phenylbutanoate (Z)-ethyl cinnamate tert-butyl dicarbonatedi-tert-butyl dicarbonate (2S,3S)-2,3-epoxy-3-phenyl-1-propanol4-[5-(cyclopropylmethoxy)-1,3-benzodioxol-4-yl]-N-[(2R,3R)-1-{4-[(4aS,8aR)-4-(3,4-dimethoxyphenyl)-1-oxo-4a,5,6,7,8,8a-hexahydrophthalazin-2(1H)-yl]piperidin-1-yl}-1-oxo-3-phenylbutan-2-yl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide 4-[5-(cyclopropylmethoxy)-1,3-benzodioxol-4-yl]-N-[(2R,3R)-1-{4-[(4aS,8aR)-4-(3,4-dimethoxyphenyl)-1-oxo-4a,5,6,7,8,8a-hexahydrophthalazin-2(1H)-yl]piperidin-1-yl}-1-oxo-3-phenylbutan-2-yl]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide 4-[2-(cyclopropylmethoxy)-5-fluoro-4-methoxyphenyl]-N-[(2R,3R)-1-{4-[(4aS,8aR)-4-(3,4-dimethoxyphenyl)-1-oxo-4a,5,6,7,8,8a-hexahydrophthalazin-2(1H)-yl]piperidin-1-yl}-1-oxo-3-phenylbutan-2-yl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide (4aS,8aR)-2-{1-[(2R,3R)-2-amino-3-phenylbutanoyl]piperidin-4-yl}-4-(3,4-dimethoxyphenyl)-4a,5,6,7,8,8a-hexahydrophthalazin-1(2H)-one

📜苯基甘油醇置于palladium On Activated Charcoal 咪唑,4-二甲氨基吡啶,Lithium Hydroxide,Sodium Azide,Jones Reagent,四丁基氟化铵,氢气,二异丁基氢化铝,Potassium Hydrogencarbonate,三乙胺,三苯基膦,偶氮二甲酸二乙酯体系中,用 四氢呋喃,乙醚,正己烷,二氯甲烷,乙酸乙酯,N,N-二甲基甲酰胺,丙酮,苯 用作溶剂,-68.0~80.0 °C,101.33 Kpa 条件下,反应 64.33H,反应生成Beta-甲基-N-{[(2-甲基-2-丙基)氧基]羰基}苯丙氨酸
参考文献:N-Boc-β-甲基苯基丙氨酸的催化不对称合成.
标题:N-Boc-β-甲基苯基丙氨酸的催化不对称合成.
摘要:已经开发了n-Boc-β-甲基苯基丙氨酸的顺式和反式非对映异构体的有效,立体发散和对映选择性的合成.从对映体纯的(2S,3S)-2,3-环氧-3-苯基-1-丙醇开始,分三步进行,包括将伯醇氧化至羧基阶段,环氧酸的开环与me(2)cucnli(2)并用甲基碘将生成的羟基酸酯化,可得到羟基酯抗10,它已以立体发散的方式转化为(2S,3R)和(2R N-Boc-β-甲基苯基丙氨酸的,3R)非对映异构体分别是syn-1和anti-1.将抗10的仲羟基活化为甲磺酸酯,然后用叠氮化钠进行亲核置换,氢解反应同时保护氨基,并用lioh皂化,得到syn-1.依次通过抗10与对硝基苯甲酸的mitsunobu反应获得,然后水解所得的对硝基苯甲酸酯水解而获得的,适用于syn-10的相同反应序列导致抗-1.两种产物均以＞ / = 99%的对映体过量获得.
Doi:10.1021/jo971178F