(S)-(N-benzyl-N-benzyloxycarbonyl)glutamic acid | 132316-96-2

• 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: (S)-(N-benzyl-N-benzyloxycarbonyl)glutamic acid
• 英文别名: (S)-N-benzyl-N-(benzyloxycarbonyl)glutamic acid；N-Benzyl-N-carbobenzyloxy-L-glutamic acid；(2S)-2-[benzyl(phenylmethoxycarbonyl)amino]pentanedioic acid
• CAS: 132316-96-2
• 化学式: C₂₀H₂₁NO₆
• 分子量: 371.39
• InChiKey: SXXYZRSVDFXXDF-KRWDZBQOSA-N

物化性质

• 沸点：
  587.5±50.0 °C(Predicted)
• 密度：
  1.315±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-(N-benzyl-N-benzyloxycarbonyl)glutamic acid 在 palladium dihydroxide 氢气 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 45.0h， 以97%的产率得到L-谷氨酸
  参考文献：
  名称：

  Enantiocontrolled Synthesis of Two Amino Acids; (S)-Glutamic Acid and (S)-2-Aminoadipic Acid

  摘要：

  分别从环戊二烯酮和环己二烯酮的手性等价物出发，开发了一种有效的对映体控制途径，制备两种酸性氨基酸（(S)-谷氨酸和(S)-2-氨基己二酸）。

  DOI：

  10.1055/s-1994-25531
• 作为产物：
  描述：

  (1R,2S,6R,7S)-tricyclo[5.2.1.0(2,6)]deca-4,8-dien-3-one 在 ruthenium trichloride 、 sodium tetrahydroborate 、 sodium periodate 、 sodium hydride 、 溶剂黄146 、 锌 作用下， 以 甲醇 、 四氯化碳 、 二苯醚 、 乙醇 、 水 、 乙腈 、 苯 为溶剂， 反应 34.5h， 生成 (S)-(N-benzyl-N-benzyloxycarbonyl)glutamic acid
  参考文献：
  名称：

  Enantiocontrolled Synthesis of Two Amino Acids; (S)-Glutamic Acid and (S)-2-Aminoadipic Acid

  摘要：

  分别从环戊二烯酮和环己二烯酮的手性等价物出发，开发了一种有效的对映体控制途径，制备两种酸性氨基酸（(S)-谷氨酸和(S)-2-氨基己二酸）。

  DOI：

  10.1055/s-1994-25531

文献信息

• Synthesis of indolidines by the 1,3-dipolar cycloaddition of azides with methylenecyclopropanes followed by cyclopropyumine rearrangement
  作者：Philip C. Heidt.‡、Stephen C. Bergmeier†、WilliAm H. Pearson‡

  DOI：10.1016/s0040-4039(00)97867-5

  日期：1990.1

  Cyclic imines 6a and 6b were obtained by the intramolecular 1,3-dipolar cycloaddition of azides with methylenecyclopropanes. Acid catalyzed rearrangement produced bicyclic (−)-enamines 7, which upon reduction provided indoilizidenes 8. A similar strategy was used for the synthesis of (−)-8a-epi-desacctoxyslaframine 16.

  通过叠氮化物的分子内1，3-偶极环加成与亚甲基环丙烷获得环亚胺6a和6b。酸催化的重排产生了双环（-）-烯胺7，还原后提供了indoilizidenes 8。类似的策略被用于合成（-）-8a-epi-desacctoxyslaframine 16。
• Synthesis of (-)-slaframine and related indolizidines
  作者：William H. Pearson、Stephen C. Bergmeier、John P. Williams

  DOI：10.1021/jo00040a045

  日期：1992.7

  An enantioselective synthesis of the indolizidine alkaloid (-)-slaframine 1 is reported. Reductive double cyclization of the azido epoxy tosylate 48 afforded the indolizidine 52, which was converted to (-)-slaframine in two steps. The cyclization substrate 48 was prepared in optically pure form from L-glutamic acid. A similar sequence starting with the epoxide 49 allowed the synthesis of (-)-1,8a-diepislaframine 56. Other routes to slaframine were investigated, often using an intramolecular cycloaddition of an azide with an alkene as a key step. Although these routes did not produce slaframine, they illustrated novel and efficient methods for the assembly of the indolizidine skeleton. Cyclization of the azidodiene 20 afforded the indolizidine 21 in one step as a single diastereomer, presumably a result of a chairlike transition state in the initial dipolar cycloaddition. Desulfurization and deprotection produced (-)-8a-epidesacetoxyslaframine 27. Cyclopropylimine rearrangement of 30 gave the indolizidine 31, which was also converted into (-)-8a-epidesacetoxyslaframine 27. Dipolar cycloaddition of 38 gave the 1-pyrroline 39, which was converted to the indolizidine 40 in one operation using Evans' double alkylation of the 1-metalloenamine derivative of 40. Attempted oxidation of 40 to the ketone 41 was unsuccessful, precluding a reductive amination approach to slaframine.
• A synthesis of (-)-slaframine and (-)-1,8a-diepislaframine
  作者：William H. Pearson、Stephen C. Bergmeier

  DOI：10.1021/jo00006a002

  日期：1991.3

  Reductive cyclization of the optically pure azido epoxides 12 and 13 afforded the indolizidines 14 and 16, which were conveted into (-)-slaframine 1 and (-)-1,8a-diepislaframine 18.
• PEARSON, WILLIAM H.;BERGMEIER, STEPHEN C., J. ORG. CHEM., 56,(1991) N, C. 1976-1978
  作者：PEARSON, WILLIAM H.、BERGMEIER, STEPHEN C.

  DOI：——

  日期：——
• Dérivés de mono (6-amino 6-désoxy)cyclodextrine substituée en position 6 par un reste d'alpha-aminoacide, leur procédé de préparation et leurs utilisations
  申请人：L'OREAL

  公开号：EP0624599B1

  公开（公告）日：1997-07-30