N-[(3S,6S,9S,11R,15S,18S,20R,21R,24S,25S)-3-[(1R)-3-amino-1-hydroxy-3-oxopropyl]-6-[(1S,2S)-1,2-dihydroxy-2-(4-hydroxyphenyl)ethyl]-11,20,21,25-tetrahydroxy-15-[(1R)-1-hydroxyethyl]-2,5,8,14,17,23-hexaoxo-1,4,7,13,16,22-hexazatricyclo[22.3.0.09,13]heptacosan-18-yl]-6-heptoxynaphthalene-2-carboxamide | 190720-22-0

• 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: N-[(3S,6S,9S,11R,15S,18S,20R,21R,24S,25S)-3-[(1R)-3-amino-1-hydroxy-3-oxopropyl]-6-[(1S,2S)-1,2-dihydroxy-2-(4-hydroxyphenyl)ethyl]-11,20,21,25-tetrahydroxy-15-[(1R)-1-hydroxyethyl]-2,5,8,14,17,23-hexaoxo-1,4,7,13,16,22-hexazatricyclo[22.3.0.09,13]heptacosan-18-yl]-6-heptoxynaphthalene-2-carboxamide
• CAS: 190720-22-0
• 化学式: C₅₂H₇₀N₈O₁₈
• 分子量: 1095.17
• InChiKey: NZUWIYIKUBABGX-PYSWRMLVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  78
• 可旋转键数：
  16
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  421
• 氢给体数：
  15
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  N-[(3S,6S,9S,11R,15S,18S,20R,21R,24S,25S)-3-[(1R)-3-amino-1-hydroxy-3-oxopropyl]-6-[(1S,2S)-1,2-dihydroxy-2-(4-hydroxyphenyl)ethyl]-11,20,21,25-tetrahydroxy-15-[(1R)-1-hydroxyethyl]-2,5,8,14,17,23-hexaoxo-1,4,7,13,16,22-hexazatricyclo[22.3.0.09,13]heptacosan-18-yl]-6-heptoxynaphthalene-2-carboxamide 在 palladium/alumina 、 Rh/Al₂O₃ 三聚氯氰 、 ammonium acetate 、 水 、 氢气 、 三氯乙酸 、 苯硼酸 作用下， 以 水 、 异丙醇 为溶剂， -30.0~25.0 ℃ 、275.79 kPa 条件下， 反应 47.5h， 生成
  参考文献：
  名称：

  Semisynthesis of an Antifungal Lipopeptide Echinocandin

  摘要：

  Compound 1 is a macrocyclic lipopeptide belonging to the echinocandin family, which has been effective in treating systemic fungal infections. In this paper, we report a unique regio-, chemo-, and stereoselective synthesis of 1 in four steps from the deacylated nucleus 3 in an impressive 83% overall yield. Highlights of this synthesis include a selective reduction of the amide to the amine and a highly stereoselective (99:1 alpha/beta) introduction of the 2-aminoethyl hemiaminal. In addition, the synthesis of the naphthoyl side chain was accomplished in three steps in 79% overall isolated yield from commercially available 6-bromo-2-naphthol.

  DOI：

  10.1021/jo9822232
• 作为产物：
  描述：

  6-溴-2-萘酚 在 palladium diacetate 、 sodium hydroxide 、 1,3-双(二苯基膦)丙烷 、 三乙胺 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 5.0~80.0 ℃ 、413.68 kPa 条件下， 反应 34.0h， 生成 N-[(3S,6S,9S,11R,15S,18S,20R,21R,24S,25S)-3-[(1R)-3-amino-1-hydroxy-3-oxopropyl]-6-[(1S,2S)-1,2-dihydroxy-2-(4-hydroxyphenyl)ethyl]-11,20,21,25-tetrahydroxy-15-[(1R)-1-hydroxyethyl]-2,5,8,14,17,23-hexaoxo-1,4,7,13,16,22-hexazatricyclo[22.3.0.09,13]heptacosan-18-yl]-6-heptoxynaphthalene-2-carboxamide
  参考文献：
  名称：

  Semisynthesis of an Antifungal Lipopeptide Echinocandin

  摘要：

  Compound 1 is a macrocyclic lipopeptide belonging to the echinocandin family, which has been effective in treating systemic fungal infections. In this paper, we report a unique regio-, chemo-, and stereoselective synthesis of 1 in four steps from the deacylated nucleus 3 in an impressive 83% overall yield. Highlights of this synthesis include a selective reduction of the amide to the amine and a highly stereoselective (99:1 alpha/beta) introduction of the 2-aminoethyl hemiaminal. In addition, the synthesis of the naphthoyl side chain was accomplished in three steps in 79% overall isolated yield from commercially available 6-bromo-2-naphthol.

  DOI：

  10.1021/jo9822232

文献信息

• Semisynthesis of an Antifungal Lipopeptide Echinocandin
  作者：Michel Journet、Dongwei Cai、Lisa M. DiMichele、David L. Hughes、Robert D. Larsen、Thomas R. Verhoeven、Paul J. Reider

  DOI：10.1021/jo9822232

  日期：1999.4.1

  Compound 1 is a macrocyclic lipopeptide belonging to the echinocandin family, which has been effective in treating systemic fungal infections. In this paper, we report a unique regio-, chemo-, and stereoselective synthesis of 1 in four steps from the deacylated nucleus 3 in an impressive 83% overall yield. Highlights of this synthesis include a selective reduction of the amide to the amine and a highly stereoselective (99:1 alpha/beta) introduction of the 2-aminoethyl hemiaminal. In addition, the synthesis of the naphthoyl side chain was accomplished in three steps in 79% overall isolated yield from commercially available 6-bromo-2-naphthol.