N-甲基-D-亮氨酸苄酯 | 89536-86-7

• 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
• 中文名称: N-甲基-D-亮氨酸苄酯
• 英文名称: H-N-Me-D-Leu-OBzl
• 英文别名: H-D-MeLeu-OBzl；(R)-Benzyl 4-methyl-2-(methylamino)pentanoate；benzyl (2R)-4-methyl-2-(methylamino)pentanoate
• CAS: 89536-86-7
• 化学式: C₁₄H₂₁NO₂
• 分子量: 235.326
• InChiKey: CXFYAORPHAAFTE-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-甲基-D-亮氨酸苄酯 在 N-甲基吗啉 、 盐酸 、 三乙酰氧基硼氢化钠 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 生成 L-lactyl-Pro-ψ(NHCH2)-N-methyl-D-leucine benzyl ester
  参考文献：
  名称：

  Structure–activity relationships of side-chain modified didemnins

  摘要：

  The synthesis and antitumor activity of a novel didemnin B analogue containing a Psi [CH2NH] amide bond surrogate between N-Me-D-Leu(7) and pro(8) are reported. The analogue shows activity (GI(50) = 4 nM) comparable to that of didemnin B (GI(50) = 13 nM) in the NCI-60 tumor cell screen. This result, along with new data from previously reported synthetic didemnin analogues, is discussed within the context of the side-chain SAR for didemnins. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00638-7
• 作为产物：
  描述：

  Boc-D-leucine benzyl ester 在 sodium hexamethyldisilazane 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 N-甲基-D-亮氨酸苄酯
  参考文献：
  名称：

  Structure–activity relationships of side-chain modified didemnins

  摘要：

  The synthesis and antitumor activity of a novel didemnin B analogue containing a Psi [CH2NH] amide bond surrogate between N-Me-D-Leu(7) and pro(8) are reported. The analogue shows activity (GI(50) = 4 nM) comparable to that of didemnin B (GI(50) = 13 nM) in the NCI-60 tumor cell screen. This result, along with new data from previously reported synthetic didemnin analogues, is discussed within the context of the side-chain SAR for didemnins. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00638-7

文献信息

• Synthesis of Cyclosporine. Part II. Synthesis of Boc-D-Ala-MeLeu-MeLeu-MeVal-OH, a part of the peptide sequence of cyclosporine, by different strategic ways and synthesis of its isomers Boc-D-Ala-MeLeu-D-MeLeu-MeVal-OH, Boc-D-MeLeu-DMeVal-OH, and Boc-D-Ala-MeLeu-MeLeu-D-MeVal-OH as reference compounds
  作者：Roland M. Wenger

  DOI：10.1002/hlca.19830660836

  日期：1983.12.14

  Boc-D-Ala-MeLeu-MeLeu-MeVal-OH (DLLL) and its isomers DLDL, DLDD and DLLD were synthesized using several different strategic approaches and a modification of the mixed pivalic anhydride method for carboxyl activation. Alternatively, the tert-butoxy-carbonyl (Boc) or benzyloxycarbonyl (Z) amino-protecting groups and the benzyloxy (OBzl) or tert-butoxy (OtBu) carboxyl-protecting groups were used to protect

  Boc-D-Ala-MeLeu-MeLeu-MeVal-OH（DLLL）及其异构体DLDL，DLDD和DLLD使用几种不同的策略方法进行了合成，并对混合新戊酸酐法进行了羧基活化修饰。或者，使用叔丁氧基羰基（Boc）或苄氧基羰基（Z）氨基保护基和苄氧基（OBzl）或叔丁氧基（Ot Bu）羧基保护基来保护反应的肽。通过监控反应温度，可以从作为肽模型的三肽DLL开始选择性地合成四肽DLLL（-20°）或四肽DLDL（+ 20°）。使用1通过H-NMR谱追踪DLL和DLD三肽的混合新戊酸酐的形成，可以证明酸酐的形成强烈依赖于温度。在−20°（几个小时）时缓慢，而在+ 20°（20至40分钟）时快。通过在-20°下工作，DLL-酸酐向更稳定的DLD-酸酐的异构化可以降至最低，而该异构化在+ 20°进行至接近完成。