(R)-dimethyl N-(benzyloxycarbonyl)pyrrolidine-2-phosphonate | 1446422-46-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-dimethyl N-(benzyloxycarbonyl)pyrrolidine-2-phosphonate
• CAS: 1446422-46-3
• 化学式: C₁₄H₂₀NO₅P
• 分子量: 313.29
• InChiKey: SWMJRGSXBYMRJG-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.23
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  65.07
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (R)-dimethyl N-(benzyloxycarbonyl)pyrrolidine-2-phosphonate 在 氢溴酸 、 溶剂黄146 作用下， 反应 2.0h， 以100%的产率得到(R)-pyrrolidine-2-phosphonic acid
  参考文献：
  名称：

  Enzymatic and chromatographic resolution procedures applied to the synthesis of the phosphoproline enantiomers

  摘要：

  The preparation of enantiomerically pure pyrrolidine-2-phosphonic acid (phosphoproline, Pro(P)) has been addressed through the synthesis of suitable racemates and subsequent resolution by independent enzyme-catalyzed and chiral HPLC methods. First, racemic phosphoproline derivatives bearing the necessary protecting groups have been synthesized in excellent global yields starting from inexpensive materials. Preparative HPLC resolution of the N-Cbz-protected aminophosphonate on a cellulose-based column allowed the isolation of enantiomerically pure enantiomers on a gram scale. Enzyme-catalyzed alkoxycarbonylation of the aminophosphonate was studied using different lipases, solvents, and carbonates. Candida antarctica lipase type A (CAL-A) provided the highest enantioselectivity when combined with benzyl 3-methoxyphenyl carbonate. (c) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2015.10.016
• 作为产物：
  描述：

  benzyl 2-(dimethoxyphosphoryl)pyrrolidine-1-carboxylate 在 250 x 20 mm Chiralpak IC column 作用下， 以 正己烷 、 氯仿 、 丙酮 为溶剂， 以909 mg的产率得到(R)-dimethyl N-(benzyloxycarbonyl)pyrrolidine-2-phosphonate
  参考文献：
  名称：

  Enzymatic and chromatographic resolution procedures applied to the synthesis of the phosphoproline enantiomers

  摘要：

  The preparation of enantiomerically pure pyrrolidine-2-phosphonic acid (phosphoproline, Pro(P)) has been addressed through the synthesis of suitable racemates and subsequent resolution by independent enzyme-catalyzed and chiral HPLC methods. First, racemic phosphoproline derivatives bearing the necessary protecting groups have been synthesized in excellent global yields starting from inexpensive materials. Preparative HPLC resolution of the N-Cbz-protected aminophosphonate on a cellulose-based column allowed the isolation of enantiomerically pure enantiomers on a gram scale. Enzyme-catalyzed alkoxycarbonylation of the aminophosphonate was studied using different lipases, solvents, and carbonates. Candida antarctica lipase type A (CAL-A) provided the highest enantioselectivity when combined with benzyl 3-methoxyphenyl carbonate. (c) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2015.10.016

文献信息

• Enantioselective Synthesis of <i>H</i>-Phosphinic Acids Bearing Natural Amino Acid Residues
  作者：Qiuli Yao、Chengye Yuan

  DOI：10.1021/jo400798f

  日期：2013.7.19

  The first systematic study on the asymmetric synthesis of H-phosphinic acids bearing natural protein amino acid residues was reported on the basis of the asymmetric addition of ethyl diethoxymethylphosphinate to N-tert-butane-sulfinyl imines. Good yields and moderate to high enantiose-lectivities were obtained. Reliable methods were developed for the elucidation of the stereochemistry of these phosphinic acids and derivatives thereof. The transformation of the side chains of these analogues was studied. Methods for the conversion of the alpha-aminophosphinates to oligopetides were reported.