Diphenylmethyl (2S)-2-hydroxy-4-methylpentanoate | 168070-01-7

• 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: Diphenylmethyl (2S)-2-hydroxy-4-methylpentanoate
• 英文别名: benzhydryl (2S)-2-hydroxy-4-methylpentanoate
• CAS: 168070-01-7
• 化学式: C₁₉H₂₂O₃
• 分子量: 298.382
• InChiKey: TXWNBOSKRNQVIC-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Diphenylmethyl (2S)-2-hydroxy-4-methylpentanoate 在 palladium on activated charcoal N-甲基吗啉 、 4-二甲氨基吡啶 、 TEA 、 氢气 、 双(2-氧代-3-恶唑烷基)次磷酰氯 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate 、 三氟乙酸 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 生成 N-((1,1-Dimethylethoxy)carbonyl)-β-Ala-O-D-Leu-L-Leu-O-L-Leu-N(Me)-L-Phe phenylmethyl ester
  参考文献：
  名称：

  Synthesis and evaluation of backbone/amide-modified analogs of leualacin

  摘要：

  Leualacin (1), a cyclic depsi-pentapeptide, and its backbone/amide-modified analogs 2-4 were synthesized. Amide analogue 3 exhibited stronger vasodilatory effects. It also strongly inhibited collagen- and arachidonic acid (AA)induced platelet aggregations with IC(50)s of 0.6 mu M and 2.0 mu M, respectively (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00038-4
• 作为产物：
  描述：

  L-alpha-羟基异己酸 、 二苯甲酮腙 在 碘苯二乙酸 、 碘 作用下， 以 二氯甲烷 为溶剂， 以81%的产率得到Diphenylmethyl (2S)-2-hydroxy-4-methylpentanoate
  参考文献：
  名称：

  Total Synthesis of the Cyclic Depsipeptide Leualacin

  摘要：

  The fungal metabolite leualacin (1), a potent calcium channel antagonist, was synthesized in 15 steps from commercially available amino acids in 25% overall yield using standard solution methods. The synthesis is general and thus would accommodate the incorporation of amino acid replacements as well as the inclusion of peptide mimics and isosteres.

  DOI：

  10.1021/jo00124a019

文献信息

• Total Synthesis of the Cyclic Depsipeptide Leualacin
  作者：Kevin L. McLaren

  DOI：10.1021/jo00124a019

  日期：1995.9

  The fungal metabolite leualacin (1), a potent calcium channel antagonist, was synthesized in 15 steps from commercially available amino acids in 25% overall yield using standard solution methods. The synthesis is general and thus would accommodate the incorporation of amino acid replacements as well as the inclusion of peptide mimics and isosteres.
• Synthesis and evaluation of backbone/amide-modified analogs of leualacin
  作者：Ming-Kuan Hu、Fu-Chu Yang、Chi-Cheun Chou、Mao-Hsiung Yen

  DOI：10.1016/s0960-894x(99)00038-4

  日期：1999.2

  Leualacin (1), a cyclic depsi-pentapeptide, and its backbone/amide-modified analogs 2-4 were synthesized. Amide analogue 3 exhibited stronger vasodilatory effects. It also strongly inhibited collagen- and arachidonic acid (AA)induced platelet aggregations with IC(50)s of 0.6 mu M and 2.0 mu M, respectively (C) 1999 Elsevier Science Ltd. All rights reserved.