N-苄氧羰基-DL-丙氨酸苄酯 | 5513-39-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: N-苄氧羰基-DL-丙氨酸苄酯
• 英文名称: N-benzyloxycarbonyl-alanine benzyl ester
• 英文别名: N-Benzyloxycarbonyl-alanin-benzylester；Benzyl N-benzyloxycarbonyl-DL-alaninate；benzyl 2-(phenylmethoxycarbonylamino)propanoate
• CAS: 5513-39-3
• 化学式: C₁₈H₁₉NO₄
• 分子量: 313.353
• InChiKey: CAFULDPKQDKWIN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  N-苄氧羰基-DL-丙氨酸苄酯 、 Thr-NHNH2 以 叔丁醇 为溶剂， 反应 2.0h， 以65%的产率得到Cbz-Ala-Thr-NHNH2
  参考文献：
  名称：

  Kinetically controlled peptide bond formation in anhydrous alcohol catalyzed by the industrial protease alcalase

  摘要：

  The industrial alkaline protease alcalase has been found to be very stable (half life > 5 days in ethanol or 2-methyl-2-propanol) and active in alcoholic solvents (except methanol). Procedures have been developed for alcalase-catalyzed, kinetically controlled peptide bond formation in anhydrous alcohol(ethanol, 2-methyl-2-propanol). Studies of the selectivity of an alcalase-catalyzed reaction show that only L-amino acid acyl donors are substrates at the p-1 subsite of alcalase; at the p-1' subsite both D- and L-amino acid nucleophiles are substrates. Other amino compounds such as benzylamine and phenylhydrazine are good nucleophiles. Studies of the effect of the water content of the reaction solution on the yield in the synthesis of Moz-Phe-Leu-NH2 showed that the 95% yield obtained in anhydrous 2-methyl-2-propanol was decreased to 48% in 2-methyl-2-propanol containing 4.86% water.

  DOI：

  10.1021/jo00051a052
• 作为产物：
  描述：

  N-CBZ-DL-丙氨酸 、 苯甲醇 在 磺酰氯 作用下， 以 四氯乙烯 为溶剂， 生成 N-苄氧羰基-DL-丙氨酸苄酯
  参考文献：
  名称：

  Taschner,E.; Wasielewski,C., Justus Liebigs Annalen der Chemie, 1961, vol. 640, p. 139 - 141

  摘要：

  DOI：

文献信息

• Diastereoselective Synthesis of β-Substituted α-Methylserines via Chelated Alanine Ester Enolates
  作者：Roland Grandel、Uli Kazmaier

  DOI：10.1002/(sici)1099-0690(199802)1998:2<409::aid-ejoc409>3.0.co;2-2

  日期：1998.2

  N-protected alanine esters with LDA, and subsequent addition of various metal salts, most likely results in the formation of chelated metal enolates. Aldol reactions of these enolates with aldehydes afford the anti isomers of α-methyl α-amino-β-hydroxy acid derivatives in a highly diastereoselectiv fashion. Best results are obtained with tin enolates of N-sulfonylated alanine esters, which give excellent

  N-保护的丙氨酸酯用LDA脱质子化，随后添加各种金属盐，最有可能导致螯合的金属烯醇化物的形成。这些烯醇化物与醛的醛醇缩合反应以高度非对映选择性的方式提供了α-甲基α-氨基-β-羟基酸衍生物的反异构体。N-磺酰化丙氨酸酯的烯醇锡可获得最佳结果，脂族和芳族醛均能获得优异的结果。使用显示出与相应的Ts-保护的酯相同的良好收率和非对映选择性的SES-保护的衍生物，可以制备游离的α-甲基丝氨酸。
• Incorporation of unnatural amino acid derivatives into a peptide bond via an oxime ester catalysed by papain or lipase
  作者：Shui-Tein Chen、Chin-Far Tsai、Kung-Tsung Wang

  DOI：10.1039/cc9960000165

  日期：——

  In the presence of an oxime in the reaction solution, papain and lipase P (Pseudomonas from Amano) catalysed the stereoselective transesterification of an N-protected amino acid or peptide ester to form an active (oxime) ester which in turn underwent peptide bond formation with several natural and unnatural amino acid derivatives (proline, N-methylglycine, N-methylalanine, α-methylphenylalanine).

  在反应溶液中存在肟的情况下，木瓜蛋白酶和脂肪酶 P（天野假单胞菌）催化 N 保护氨基酸或肽酯的立体选择性酯交换反应，形成活性（肟）酯，活性酯又与几种天然和非天然氨基酸衍生物（脯氨酸、N-甲基甘氨酸、N-甲基丙氨酸、α-甲基苯丙氨酸）形成肽键。
• Cleavage of N-Carbobenzoxy Groups by dry Hydrogen Bromide and Hydrogen Chloride
  作者：Dov Ben-Ishai、Arieh Berger

  DOI：10.1021/jo50012a002

  日期：1952.12
• Grandel, Roland; Kazmaier, Uli; Nuber, Bernhard, Liebigs Annalen, 1996, # 7, p. 1143 - 1150
  作者：Grandel, Roland、Kazmaier, Uli、Nuber, Bernhard

  DOI：——

  日期：——
• US8476011B1
  申请人：——

  公开号：US8476011B1

  公开（公告）日：2013-07-02