N-[(tert-butoxy)carbonyl]-D-alanyl-N-methyl-L-leucyl-N-methyl-L-leucyl-N-methyl-L-valyl-(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-(methylamino)oct-6-enoyl-(2S)-2-aminobutanoyl-N-methylglycyl-N-methyl-L-leucine | 1252617-22-3

• 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-[(tert-butoxy)carbonyl]-D-alanyl-N-methyl-L-leucyl-N-methyl-L-leucyl-N-methyl-L-valyl-(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-(methylamino)oct-6-enoyl-(2S)-2-aminobutanoyl-N-methylglycyl-N-methyl-L-leucine
• 英文别名: Boc-D-Ala-N(Me)Leu-N(Me)Leu-N(Me)Val-N(Me)Bmt(E)-Abu-Sar-N(Me)Leu-OH；(2S)-2-[[2-[[(2S)-2-[[(E,2S,3R,4R)-3-hydroxy-4-methyl-2-[methyl-[(2S)-3-methyl-2-[methyl-[(2S)-4-methyl-2-[methyl-[(2S)-4-methyl-2-[methyl-[(2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]pentanoyl]amino]pentanoyl]amino]butanoyl]amino]oct-6-enoyl]amino]butanoyl]-methylamino]acetyl]-methylamino]-4-methylpentanoic acid
• CAS: 1252617-22-3
• 化学式: C₅₂H₉₄N₈O₁₂
• 分子量: 1023.36
• InChiKey: FLGNZXOOJREHLX-PDHWHKGOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  72
• 可旋转键数：
  30
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  247
• 氢给体数：
  4
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  4,4,4,4',4',4'-hexafluoro-N-(2-hydroxyethoxy)-D-valyl-N-methyl-L-leucine-L-alanine tert-butyl ester 、 N-[(tert-butoxy)carbonyl]-D-alanyl-N-methyl-L-leucyl-N-methyl-L-leucyl-N-methyl-L-valyl-(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-(methylamino)oct-6-enoyl-(2S)-2-aminobutanoyl-N-methylglycyl-N-methyl-L-leucine 在 4-二甲氨基吡啶 、 N-羟基-7-氮杂苯并三氮唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 336.0h， 以95%的产率得到N-[(tert-butoxy)carbonyl]-D-alanyl-N-methyl-L-leucyl-N-methyl-L-leucyl-N-methyl-L-valyl-(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-(methylamino)oct-6-enoyl-(2S)-2-aminobutanoyl-N-methylglycyl-N-methyl-L-leucyloxy-Ψ(O-CH2)-ethoxy-Ψ(O-NH)-4,4,4,4',4',4'-hexafluoro-D-valyl-N-methyl-L-leucyl-L-alanine tert-butyl ester
  参考文献：
  名称：

  Stereoselective Synthesis of [5-[4,4,4,4′,4′,4′-Hexafluoro-N-(2-hydroxyethoxy)-D-valine]]- and [5-[4,4,4,4′,4′,4′-Hexafluoro-N-(2-hydroxyethoxy)-L-valine]cyclosporin A

  摘要：

  AbstractAddition of various amines to the 3,3‐bis(trifluoromethyl)acrylamides 10a and 10b gave the tripeptides 11a–11f, mostly as mixtures of epimers (Scheme 3). The crystalline tripeptide 11f2 was found to be the N‐terminal (2‐hydroxyethoxy)‐substituted (R,S,S)‐ester HOCH2CH2O‐D‐Val(F6)‐MeLeu‐Ala‐OtBu by X‐ray crystallography. The C‐terminal‐protected tripeptide 11f2 was condensed with the N‐terminus octapeptide 2b to the depsipeptide 12a which was thermally rearranged to the undecapeptide 13a (Scheme 4). The condensation of the epimeric tripeptide 11f1 with the octapeptide 2b gave the undecapeptide 13b directly. The undecapeptides 13a and 13b were fully deprotected and cyclized to the [5‐[4,4,4,4′,4′,4′‐hexafluoro‐N‐(2‐hydroxyethoxy)‐D‐valine]]‐ and [5‐[4,4,4,4′,4′,4′‐hexafluoro‐N‐(2‐hydroxyethoxy)‐L‐valine]]cyclosporins 14a and 14b, respectively (Scheme 5). Rate differences observed for the thermal rearrangements of 12a to 13a and of 12b to 13b are discussed.

  DOI：

  10.1002/hlca.201000175
• 作为产物：
  描述：

  在 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以44%的产率得到N-[(tert-butoxy)carbonyl]-D-alanyl-N-methyl-L-leucyl-N-methyl-L-leucyl-N-methyl-L-valyl-(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-(methylamino)oct-6-enoyl-(2S)-2-aminobutanoyl-N-methylglycyl-N-methyl-L-leucine
  参考文献：
  名称：

  Stereoselective Synthesis of [5-[4,4,4,4′,4′,4′-Hexafluoro-N-(2-hydroxyethoxy)-D-valine]]- and [5-[4,4,4,4′,4′,4′-Hexafluoro-N-(2-hydroxyethoxy)-L-valine]cyclosporin A

  摘要：

  AbstractAddition of various amines to the 3,3‐bis(trifluoromethyl)acrylamides 10a and 10b gave the tripeptides 11a–11f, mostly as mixtures of epimers (Scheme 3). The crystalline tripeptide 11f2 was found to be the N‐terminal (2‐hydroxyethoxy)‐substituted (R,S,S)‐ester HOCH2CH2O‐D‐Val(F6)‐MeLeu‐Ala‐OtBu by X‐ray crystallography. The C‐terminal‐protected tripeptide 11f2 was condensed with the N‐terminus octapeptide 2b to the depsipeptide 12a which was thermally rearranged to the undecapeptide 13a (Scheme 4). The condensation of the epimeric tripeptide 11f1 with the octapeptide 2b gave the undecapeptide 13b directly. The undecapeptides 13a and 13b were fully deprotected and cyclized to the [5‐[4,4,4,4′,4′,4′‐hexafluoro‐N‐(2‐hydroxyethoxy)‐D‐valine]]‐ and [5‐[4,4,4,4′,4′,4′‐hexafluoro‐N‐(2‐hydroxyethoxy)‐L‐valine]]cyclosporins 14a and 14b, respectively (Scheme 5). Rate differences observed for the thermal rearrangements of 12a to 13a and of 12b to 13b are discussed.

  DOI：

  10.1002/hlca.201000175