methyl (3R)-3-aminohexadecanoate | 331866-80-9

• 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: methyl (3R)-3-aminohexadecanoate
• CAS: 331866-80-9
• 化学式: C₁₇H₃₅NO₂
• 分子量: 285.47
• InChiKey: CTVINBNSGJBIBG-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  20
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (3R)-3-aminohexadecanoate 在 lithium hydroxide 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 6.0h， 生成 (3R)-3-[[(2S)-5-[(2-methylpropan-2-yl)oxycarbonylamino]-2-(phenylmethoxycarbonylamino)pentanoyl]amino]hexadecanoic acid
  参考文献：
  名称：

  An expedient synthesis of the amide analog of the potent antifungal lipopeptidolactone FR901469

  摘要：

  An expedient synthesis of the lactam analog (2) of the 40-membered lipopeptidolactone antifungal antibiotic, FR901469 (1), is described. The key steps in this synthesis are a novel biotransformation of the natural product to produce the highly versatile linear peptide building block 3, and efficient formation of the 40-membered ring by macrolactamization under high-dilution conditions. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)02047-5
• 作为产物：
  描述：

  (E)-甲基酯,2-十六碳烯酸 在 palladium dihydroxide 氢气 作用下， 以 四氢呋喃 、 甲醇 、 溶剂黄146 、 乙酸乙酯 为溶剂， 反应 7.0h， 生成 methyl (3R)-3-aminohexadecanoate
  参考文献：
  名称：

  An expedient synthesis of the amide analog of the potent antifungal lipopeptidolactone FR901469

  摘要：

  An expedient synthesis of the lactam analog (2) of the 40-membered lipopeptidolactone antifungal antibiotic, FR901469 (1), is described. The key steps in this synthesis are a novel biotransformation of the natural product to produce the highly versatile linear peptide building block 3, and efficient formation of the 40-membered ring by macrolactamization under high-dilution conditions. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)02047-5

文献信息

• An expedient synthesis of the amide analog of the potent antifungal lipopeptidolactone FR901469
  作者：David Barrett、Akira Tanaka、Akihiko Fujie、Nobuharu Shigematsu、Michizane Hashimoto、Seiji Hashimoto

  DOI：10.1016/s0040-4039(00)02047-5

  日期：2001.1

  An expedient synthesis of the lactam analog (2) of the 40-membered lipopeptidolactone antifungal antibiotic, FR901469 (1), is described. The key steps in this synthesis are a novel biotransformation of the natural product to produce the highly versatile linear peptide building block 3, and efficient formation of the 40-membered ring by macrolactamization under high-dilution conditions. (C) 2001 Elsevier Science Ltd. All rights reserved.