N-<(benzyloxy)carbonyl>-L-(2-benzyl-5S-isoxazolidin-5-yl)glycine benzyl ester | 130096-71-8

• 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: N-<(benzyloxy)carbonyl>-L-(2-benzyl-5S-isoxazolidin-5-yl)glycine benzyl ester
• 英文别名: N-[(benzyloxy)carbonyl]-L-(2-benzyl-5S-isoxazolidin-5-yl)glycine benzyl ester；benzyl (2S)-2-[(5S)-2-benzyl-1,2-oxazolidin-5-yl]-2-(phenylmethoxycarbonylamino)acetate
• CAS: 130096-71-8
• 化学式: C₂₇H₂₈N₂O₅
• 分子量: 460.53
• InChiKey: SBTOEXNNGUIWCK-DQEYMECFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.23
• 重原子数：
  34.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  77.1
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  N-<(benzyloxy)carbonyl>-L-(2-benzyl-5S-isoxazolidin-5-yl)glycine benzyl ester 在 氢溴酸 、 溶剂黄146 作用下， 反应 0.5h， 以66%的产率得到L-(2-benzyl-5R-isoxazolidin-5-yl)glycin benzyl ester
  参考文献：
  名称：

  Stereochemical correlation of proclavaminic acid and syntheses of erythro- and threo-L-.beta.-hydroxyornithine from an improved vinylglycine synthon

  摘要：

  The Hanessian method to prepare the N-Cbz-L-vinylglycine methyl ester has been improved to obtain reproducibility an alternately protected version of this useful synthon in optically pure, crystalline form. A nitrone cycloaddition route has been developed to synthesize erythro- and threo-L-beta-hydroxyornithine having stereoisomeric purities of > 99%. A parallel route described recently, proceeding from Hanessian's methyl vinlglycinate, gives these oxidatively modified alpha-amino acids in inferior enantiomeric excess owing to partial racemization that occurs in the oxidative decarboxylation to the protected vinylglycines themselves. The intermediate isoxazolidine generated in the present synthesis was separately converted to proclavaminic acid, a key intermediate in the biosynthesis of the beta-lactamase inhibitor clavulanic acid, and its absolute configuration was established as L-threo by unambiguous correlation to L-glutamic acid.

  DOI：

  10.1021/jo00002a045
• 作为产物：
  描述：

  Cbz-L-谷氨酸 1-苄酯 在 lead(IV) acetate 、 copper diacetate 作用下， 以 乙醚 、 苯 为溶剂， 反应 33.0h， 生成 N-<(benzyloxy)carbonyl>-L-(2-benzyl-5S-isoxazolidin-5-yl)glycine benzyl ester
  参考文献：
  名称：

  Stereochemical correlation of proclavaminic acid and syntheses of erythro- and threo-L-.beta.-hydroxyornithine from an improved vinylglycine synthon

  摘要：

  The Hanessian method to prepare the N-Cbz-L-vinylglycine methyl ester has been improved to obtain reproducibility an alternately protected version of this useful synthon in optically pure, crystalline form. A nitrone cycloaddition route has been developed to synthesize erythro- and threo-L-beta-hydroxyornithine having stereoisomeric purities of > 99%. A parallel route described recently, proceeding from Hanessian's methyl vinlglycinate, gives these oxidatively modified alpha-amino acids in inferior enantiomeric excess owing to partial racemization that occurs in the oxidative decarboxylation to the protected vinylglycines themselves. The intermediate isoxazolidine generated in the present synthesis was separately converted to proclavaminic acid, a key intermediate in the biosynthesis of the beta-lactamase inhibitor clavulanic acid, and its absolute configuration was established as L-threo by unambiguous correlation to L-glutamic acid.

  DOI：

  10.1021/jo00002a045

文献信息

• Investigation of the stereospecificity of clavaminic acid synthase in the desaturation of dihydroclavaminic acid to clavaminic acid
  作者：Jack E. Baldwin、Robert M. Adlington、Nicholas P. Crouch、David J. Drake、Yoshiyuki Fujishima、Stephen W. Elson、Keith H. Baggaley

  DOI：10.1039/c39940001133

  日期：——

  Incubations of (4R)- and (4S)-[4-2H1]-proclavaminic acid with clavaminic acid synthase resulted in the stereospecific removal of the deuterium and hydrogen respectively from C-4, in their conversions to clavaminic acid, suggesting an enzyme catalysed syn-eliminaion for the desaturation of dihydroclavaminic acid to clavaminic acid.

  （4R）和（4S）-［4-2H1］-前克拉瓦酸与克拉瓦酸合成酶反应时，分别在转化为克拉瓦酸的过程中，从C-4上立体特异性地去除了氘和氢，这表明在双氢克拉瓦酸转化为克拉瓦酸的过程中，酶催化了一个同步消除反应。
• KROL, WALTER J.;MAO, SHI-SHAN;STEELE, DIANA L.;TOWNSEND, CRAIG A., J. ORG. CHEM., 56,(1991) N, C. 728-731
  作者：KROL, WALTER J.、MAO, SHI-SHAN、STEELE, DIANA L.、TOWNSEND, CRAIG A.

  DOI：——

  日期：——