72086-72-7

基本信息
BOC-谷氨酸- Α-甲酯
N-叔丁氧羰基-L-谷氨酸 1-甲酯
N-BOC-L-谷氨酸-ALPHA-甲酯
BOC-L-GLU-OME
BOC-GLUTAMIC ACID-OME
BOC-GLU-OME USP/EP/BP
(Tert-Butoxy)Carbonyl Glu-OMe
Boc-L-glutamicacida-methylester
BOC-L-GLUTAMIC ACID METHYL ESTER
Boc-L-Glutamic Acid 5-Methyl Ester
Boc-L-glutamic acid 1-methyl ester
Boc-L-glutamic acid α-methyl ester
物理化学性质
制备方法

59279-58-2

72086-72-7
以(S)-5-苄基-2-((叔丁氧基羰基)氨基)戊二酸甲酯为原料合成(S)-4-((叔丁氧基羰基)氨基)-5-甲氧基-5-氧代戊酸的一般步骤如下:将(S)-5-苄基-2-((叔丁氧基羰基)氨基)戊二酸甲酯(4.95 g,14.09 mmol)溶于50 mL圆底烧瓶中的甲醇(20 mL)中,并在氮气保护下加入10%钯/碳催化剂。随后,用氮气和氢气交替吹扫反应容器三次。在氢气氛围及大气压力下,将反应混合物搅拌6小时。反应完成后,通过过滤移除催化剂,并将滤液浓缩,得到目标化合物(S)-4-((叔丁氧基羰基)氨基)-5-甲氧基-5-氧代戊酸,为无色胶状液体(3.5 g,产率96%)。产物的比旋光度[α]21D = +7(c 0.1,CHCl3)。核磁共振氢谱(1H NMR,CDCl3,400 MHz)δ:1.4(s,9H),1.87-1.96(m,1H),2.12-2.15(m,1H),2.35-2.49(m,2H),3.71(s,3H),4.31-4.33(d,1H,J = 4.64 Hz),5.24-5.27(d,1H,J = 8.16 Hz),10.19(s,1H)。核磁共振碳谱(13C NMR,CDCl3,100 MHz)δ:27.5,28.2,30.0,52.4,52.8,80.2,155.5,172.8,177.7。红外光谱(IR,KBr)νmax:3346,2979,1719,1520,1439,1394,1369,1216,1167,1057,1029,879,853,816,780,596,463 cm-1。
参考文献:
[1] Tetrahedron Letters, 1998, vol. 39, # 15, p. 2099 - 2102
[2] Organic and Biomolecular Chemistry, 2007, vol. 5, # 9, p. 1459 - 1465
[3] Chemical Communications, 2005, # 37, p. 4652 - 4654
[4] Tetrahedron Letters, 2014, vol. 55, # 14, p. 2274 - 2276
[5] Heterocycles, 2015, vol. 90, # 2, p. 1309 - 1316