({(S)-2-[((S)-2-Amino-propyl)-tert-butoxycarbonylmethyl-amino]-1-methyl-ethyl}-tert-butoxycarbonylmethyl-amino)-acetic acid tert-butyl ester | 171557-43-0

• 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)-2-[((S)-2-Amino-propyl)-tert-butoxycarbonylmethyl-amino]-1-methyl-ethyl}-tert-butoxycarbonylmethyl-amino)-acetic acid tert-butyl ester
• 英文别名: tert-butyl 2-[[(2S)-2-aminopropyl]-[(2S)-2-[bis[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]amino]propyl]amino]acetate
• CAS: 171557-43-0
• 化学式: C₂₄H₄₇N₃O₆
• 分子量: 473.654
• InChiKey: XDGHCYYOQHVHCR-ROUUACIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  33
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  benzyl glycolate triflate 、 ({(S)-2-[((S)-2-Amino-propyl)-tert-butoxycarbonylmethyl-amino]-1-methyl-ethyl}-tert-butoxycarbonylmethyl-amino)-acetic acid tert-butyl ester 在 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 16.0h， 以87%的产率得到[((S)-2-{[(S)-2-(Bis-benzyloxycarbonylmethyl-amino)-propyl]-tert-butoxycarbonylmethyl-amino}-1-methyl-ethyl)-tert-butoxycarbonylmethyl-amino]-acetic acid tert-butyl ester
  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：

  tert-butyl 2-[[(2S)-2-[bis[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]amino]propyl]-(4-methylphenyl)sulfonylamino]acetate 在 2,6-二甲基吡啶 、 四乙基溴化铵 、 一水合肼 作用下， 以 乙腈 为溶剂， 反应 8.0h， 生成 ({(S)-2-[((S)-2-Amino-propyl)-tert-butoxycarbonylmethyl-amino]-1-methyl-ethyl}-tert-butoxycarbonylmethyl-amino)-acetic acid tert-butyl ester
  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