methyl (S)-2-benzyloxycarbonylamino-6-diazo-5-oxohexanoate | 15366-19-5

• 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
• 英文名称: methyl (S)-2-benzyloxycarbonylamino-6-diazo-5-oxohexanoate
• 英文别名: 6-diazo-5-oxo-N-Z-L-norleucine-OMe；methyl (2S)-6-diazo-5-oxo-2-(phenylmethoxycarbonylamino)hexanoate
• CAS: 15366-19-5
• 化学式: C₁₅H₁₇N₃O₅
• 分子量: 319.317
• InChiKey: KOTORYBMVKKUIL-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  83.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (S)-2-benzyloxycarbonylamino-6-diazo-5-oxohexanoate 生成 L-2-氨基己二酸
  参考文献：
  名称：

  苄氧羰基谷氨酸酐与重氮甲烷的反应

  摘要：

  DOI：

  10.1016/s0040-4039(01)83767-9
• 作为产物：
  描述：

  N²-benzyloxycarbonyl-L-glutamine methyl ester 在 亚硝酸特丁酯 作用下， 以 乙醚 、 乙腈 为溶剂， 反应 1.5h， 生成 methyl (S)-2-benzyloxycarbonylamino-6-diazo-5-oxohexanoate
  参考文献：
  名称：

  An efficient route to the α-methyl ester ofL-glutamic acid, and its conversion into cis-5-hydroxy-L-pipecolic acid

  摘要：

  The treatment of the N-benzyloxycarbonyl alpha-methyl esters of L-glutamine or L-asparagine with tert-butyl nitrite in refluxing acetonitrile results-in selective hydrolysis of the amide group, giving optically pure Z-Glu-OMe (74%) or Z-Asp-OMe (88%); these are versatile chiral building blocks, and an efficient synthesis of cis-5-hydroxy-L pipecolic acid from Z-Glu-OMe is described.

  DOI：

  10.1039/cc9960000349

文献信息

• Cleavage of benzyloxycarbonyl-5-oxazolidinones to α-benzyloxycarbonylamino-α-alkyl esters by alcohols and sodium hydrogen carbonate
  作者：Pietro Allevi、Giuliana Cighetti、Mario Anastasia

  DOI：10.1016/s0040-4039(01)00971-6

  日期：2001.7

  The reaction of benzyloxycarbonyl-5-oxazolidinones with alcohols and sodium hydrogen carbonate to afford the corresponding benzyloxycarbonyl esters is described.

  描述了苄氧羰基-5-恶唑烷酮与醇和碳酸氢钠的反应，得到相应的苄氧羰基酯。
• Pettit, Georeg R.; Nelson, Paul S., Canadian Journal of Chemistry, 1986, vol. 64, p. 2097 - 2102
  作者：Pettit, Georeg R.、Nelson, Paul S.

  DOI：——

  日期：——
• Chiral synthesis of 5-hydroxy-(L)-pipecolic acids from (L)-glutamic acid
  作者：Patrick D Bailey、Justin S Bryans

  DOI：10.1016/s0040-4039(00)86719-2

  日期：——
• Synthesis of 5-oxo-l-pipecolic acid derivatives by rhodium(II) acetate catalyzed cyclization of diazoketones
  作者：Kwang-Youn Ko、Kee-In Lee、Wan-Loo Kim

  DOI：10.1016/s0040-4039(00)61009-2

  日期：1992.10

  A convenient synthesis of 5-oxo-L-pipecolic acid derivatives is described. The key step involves the rhodium(II) acetate catalyzed N-H insertion reaction of diazoketones, which are derived from L-glutamic acid.
• Synthesis of all four possible stereoisomers of 5-hydroxylysine
  作者：Pietro Allevi、Mario Anastasia

  DOI：10.1016/s0957-4166(00)00281-0

  日期：2000.8

  A simple protocol for the transformation of L- and D-glutamic acids into the enantiopure forms of all four isomers of 5-hydroxylysine is described. (C) 2000 Elsevier Science Ltd. All rights reserved.