6-O-benzyl 2-O-methyl (1R,2S,5S)-4-oxo-3-oxa-6-azabicyclo[3.1.0]hexane-2,6-dicarboxylate | 175656-08-3

• 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
• 英文名称: 6-O-benzyl 2-O-methyl (1R,2S,5S)-4-oxo-3-oxa-6-azabicyclo[3.1.0]hexane-2,6-dicarboxylate
• CAS: 175656-08-3
• 化学式: C₁₄H₁₃NO₆
• 分子量: 291.26
• InChiKey: MEHYAONBWUVPKM-JYYPDINASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  81.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-O-benzyl 2-O-methyl (1R,2S,5S)-4-oxo-3-oxa-6-azabicyclo[3.1.0]hexane-2,6-dicarboxylate 在 三氟化硼乙醚 、 silica gel 作用下， 反应 2.0h， 生成 methyl (2S,3S,4S)-3-methoxy-5-oxo-4-(phenylmethoxycarbonylamino)oxolane-2-carboxylate
  参考文献：
  名称：

  Synthesis of Optically Pure 3,4-Disubstituted l-Glutamates from a Novel 2,3-Aziridino-γ-lactone 4-Carboxylate Derivative

  摘要：

  The synthesis of the N-acetyl and N-Cbz derivatives of (1S,4S,5R)-4-(methoxycarbonyl)-3-oxa-6-azabicyclo[3.1.0]hexan-2-one (24 and 27, respectively) from D-ribose is described. While compound 24 reacted with methanol in the presence of boron trifluoride etherate to give the novel 2,3-iminoglutamate derivative 28, compound 27 afforded, under the same conditions, the 4(S)-hydroxy-3(S)methoxy-L-glutamate 31. Similarly, reaction of 27 with ethanol and benzyl alcohol gave the corresponding 3(S)-ethoxy and 3(S)-(benzyloxy) analogues of 31. This represents the first example of the use of a carbohydrate for the preparation of L-glutamate derivatives as well as the first example of a stereocontrolled synthesis of glutamate analogues dissymmetrically substituted at the beta,gamma-positions.

  DOI：

  10.1021/jo951983z
• 作为产物：
  描述：

  methyl (2S,3S,4R)-3-azido-5-[tert-butyl(dimethyl)silyl]oxy-4-(4-methylphenyl)sulfonyloxyoxolane-2-carboxylate 在 四丙基高钌酸铵 、 4 A molecular sieve 、 四丁基氟化铵 、 N-甲基吗啉氧化物 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 5.5h， 生成 6-O-benzyl 2-O-methyl (1R,2S,5S)-4-oxo-3-oxa-6-azabicyclo[3.1.0]hexane-2,6-dicarboxylate
  参考文献：
  名称：

  Synthesis of Optically Pure 3,4-Disubstituted l-Glutamates from a Novel 2,3-Aziridino-γ-lactone 4-Carboxylate Derivative

  摘要：

  The synthesis of the N-acetyl and N-Cbz derivatives of (1S,4S,5R)-4-(methoxycarbonyl)-3-oxa-6-azabicyclo[3.1.0]hexan-2-one (24 and 27, respectively) from D-ribose is described. While compound 24 reacted with methanol in the presence of boron trifluoride etherate to give the novel 2,3-iminoglutamate derivative 28, compound 27 afforded, under the same conditions, the 4(S)-hydroxy-3(S)methoxy-L-glutamate 31. Similarly, reaction of 27 with ethanol and benzyl alcohol gave the corresponding 3(S)-ethoxy and 3(S)-(benzyloxy) analogues of 31. This represents the first example of the use of a carbohydrate for the preparation of L-glutamate derivatives as well as the first example of a stereocontrolled synthesis of glutamate analogues dissymmetrically substituted at the beta,gamma-positions.

  DOI：

  10.1021/jo951983z

文献信息

• Enantiospecific synthesis of 3,4-disubstituted glutamic acids via controlled stepwise ring-opening of 2,3-aziridino-γ-lactone
  作者：Zhaohua Yan、Robert Weaving、Philippe Dauban、Robert H. Dodd

  DOI：10.1016/s0040-4039(02)01762-8

  日期：2002.10

  The preparation of enantiomerically pure 3,4-disubstituted glutamic acids is described starting from D-ribose. This preparation involved the use of a 2,3-aziridino-gamma-lactone whose reactivity towards nucleophiles could be efficiently controlled to allow selective functionalization at the beta-position. A key step of the strategy was a titanate-mediated transesterification of a dimethyl ester into a dibenzyl analogue, allowing efficient deprotection to the free amino acid by hydrogenolysis. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Synthesis of Optically Pure 3,4-Disubstituted <scp>l</scp>-Glutamates from a Novel 2,3-Aziridino-γ-lactone 4-Carboxylate Derivative
  作者：Philippe Dauban、Angèle Chiaroni、Claude Riche、Robert H. Dodd

  DOI：10.1021/jo951983z

  日期：1996.1.1

  The synthesis of the N-acetyl and N-Cbz derivatives of (1S,4S,5R)-4-(methoxycarbonyl)-3-oxa-6-azabicyclo[3.1.0]hexan-2-one (24 and 27, respectively) from D-ribose is described. While compound 24 reacted with methanol in the presence of boron trifluoride etherate to give the novel 2,3-iminoglutamate derivative 28, compound 27 afforded, under the same conditions, the 4(S)-hydroxy-3(S)methoxy-L-glutamate 31. Similarly, reaction of 27 with ethanol and benzyl alcohol gave the corresponding 3(S)-ethoxy and 3(S)-(benzyloxy) analogues of 31. This represents the first example of the use of a carbohydrate for the preparation of L-glutamate derivatives as well as the first example of a stereocontrolled synthesis of glutamate analogues dissymmetrically substituted at the beta,gamma-positions.