(2R)-2-[bis[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]amino]propanoic acid | 171557-09-8

• 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: (2R)-2-[bis[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]amino]propanoic acid
• CAS: 171557-09-8
• 化学式: C₁₅H₂₇NO₆
• 分子量: 317.382
• InChiKey: WZDRKRPROJPOCI-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  22
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  93.1
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2R)-2-[bis[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]amino]propanoic acid 在 N-甲基吗啉 、 盐酸 、 硼烷四氢呋喃络合物 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 7.25h， 生成 {[(R)-2-(Bis-carboxymethyl-amino)-propyl]-[(S)-2-(bis-carboxymethyl-amino)-propyl]-amino}-acetic acid; hydrochloride
  参考文献：
  名称：

  Stereocontrolled Synthesis of DTPA Analogs Branched in the Ethylene Unit

  摘要：

  Stereochemically controlled synthesis of diethylenetriaminepentaacetic acid (DTPA) analogues substituted on the ethylene backbones with methyl groups, the chiral center a to the terminal nitrogen being derived from (S)- or (R)-alanine, has been achieved. The key intermediate (S)-propylenediaminetriacetic acid triester was synthesized via selective detosylation of the alkylation product derived from (S)-alanine and tert-butyl glycinate. Attaching the remaining modified alanine (or glycine) fragment through acyl coupling and then selective reduction of the amide followed by hydrolysis of the esters afforded the substituted DTPA analogues. Ester differentiation has been accomplished through alkylation rather than acylation of the (S)-propylenediaminetriacetic acid triester. A byproduct from this alkylation is the oxazoloisoindole formed by internal alkylation of the oxygen of the phthaloyl protecting group. Phthaloyl deprotection followed by dialkylation afforded the ester-differentiated (S,S)-dipropylenetriaminepentaacetic esters. The enantiomeric purity of the chiral intermediates (S)-alaninol and (S)-propylenediamines were determined by HPLC using epimeric standards.

  DOI：

  10.1021/jo00126a059
• 作为产物：
  描述：

  碘乙酸叔丁酯 在 palladium on activated charcoal pH 7.0 phosphate buffer 、 氢气 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 80.0h， 生成 (2R)-2-[bis[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]amino]propanoic acid
  参考文献：
  名称：

  Stereocontrolled Synthesis of DTPA Analogs Branched in the Ethylene Unit

  摘要：

  Stereochemically controlled synthesis of diethylenetriaminepentaacetic acid (DTPA) analogues substituted on the ethylene backbones with methyl groups, the chiral center a to the terminal nitrogen being derived from (S)- or (R)-alanine, has been achieved. The key intermediate (S)-propylenediaminetriacetic acid triester was synthesized via selective detosylation of the alkylation product derived from (S)-alanine and tert-butyl glycinate. Attaching the remaining modified alanine (or glycine) fragment through acyl coupling and then selective reduction of the amide followed by hydrolysis of the esters afforded the substituted DTPA analogues. Ester differentiation has been accomplished through alkylation rather than acylation of the (S)-propylenediaminetriacetic acid triester. A byproduct from this alkylation is the oxazoloisoindole formed by internal alkylation of the oxygen of the phthaloyl protecting group. Phthaloyl deprotection followed by dialkylation afforded the ester-differentiated (S,S)-dipropylenetriaminepentaacetic esters. The enantiomeric purity of the chiral intermediates (S)-alaninol and (S)-propylenediamines were determined by HPLC using epimeric standards.

  DOI：

  10.1021/jo00126a059

文献信息

• Stereocontrolled Synthesis of DTPA Analogs Branched in the Ethylene Unit
  作者：Christopher W. Grote、Dong Jin Kim、Henry Rapoport

  DOI：10.1021/jo00126a059

  日期：1995.10

  Stereochemically controlled synthesis of diethylenetriaminepentaacetic acid (DTPA) analogues substituted on the ethylene backbones with methyl groups, the chiral center a to the terminal nitrogen being derived from (S)- or (R)-alanine, has been achieved. The key intermediate (S)-propylenediaminetriacetic acid triester was synthesized via selective detosylation of the alkylation product derived from (S)-alanine and tert-butyl glycinate. Attaching the remaining modified alanine (or glycine) fragment through acyl coupling and then selective reduction of the amide followed by hydrolysis of the esters afforded the substituted DTPA analogues. Ester differentiation has been accomplished through alkylation rather than acylation of the (S)-propylenediaminetriacetic acid triester. A byproduct from this alkylation is the oxazoloisoindole formed by internal alkylation of the oxygen of the phthaloyl protecting group. Phthaloyl deprotection followed by dialkylation afforded the ester-differentiated (S,S)-dipropylenetriaminepentaacetic esters. The enantiomeric purity of the chiral intermediates (S)-alaninol and (S)-propylenediamines were determined by HPLC using epimeric standards.