(10R,12S)-N-[(3S,6S,9S,11R,15S,18S,20R,21R,24S,25S)-3-[(1R)-3-amino-1-hydroxypropyl]-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]-10,12-dimethyltetradecanamide | 150283-04-8

• 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: (10R,12S)-N-[(3S,6S,9S,11R,15S,18S,20R,21R,24S,25S)-3-[(1R)-3-amino-1-hydroxypropyl]-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]-10,12-dimethyltetradecanamide
• CAS: 150283-04-8
• 化学式: C₅₀H₈₂N₈O₁₆
• 分子量: 1051.25
• InChiKey: OXVVQYCKEAJWFA-CRUNQLHUSA-N

物化性质

• 沸点：
  1396.2±65.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  74
• 可旋转键数：
  20
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  394
• 氢给体数：
  15
• 氢受体数：
  17

制备方法与用途

Echinocandin B0是一种化合物。

反应信息

• 作为反应物：
  描述：

  (10R,12S)-N-[(3S,6S,9S,11R,15S,18S,20R,21R,24S,25S)-3-[(1R)-3-amino-1-hydroxypropyl]-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]-10,12-dimethyltetradecanamide 在 三氟乙酸 作用下， 以 乙腈 为溶剂， 反应 16.5h， 生成
  参考文献：
  名称：

  Synthesis of the Antifungal β-1,3-Glucan Synthase Inhibitor CANCIDAS (Caspofungin Acetate) from Pneumocandin B₀

  摘要：

  A novel three-step synthesis of the highly functionalized antifungal agent CANCIDAS (caspofungin acetate, 2) is described, starting from the natural product pneumocandin B-0 (1). The highlights of the synthesis include a stereoselective formation of a phenylthioaminal, a remarkable chemoselective, high-yielding, one-step borane reduction of a primary amide, and a stereoselective substitution of the phenylthioaminal with ethylenediamine producing 2 in a 45% overall yield.

  DOI：

  10.1021/jo062008i
• 作为产物：
  描述：

  (10R,12S)-N-[(3S,6S,9S,11R,15S,18S,20R,21R,24S,25S)-3-[(1R)-2-cyano-1-hydroxyethyl]-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]-10,12-dimethyltetradecanamide 在 palladium 10% on activated carbon ammonium acetate 、 氢气 作用下， 以 水 、 溶剂黄146 、 异丙醇 为溶剂， 反应 28.0h， 以92%的产率得到(10R,12S)-N-[(3S,6S,9S,11R,15S,18S,20R,21R,24S,25S)-3-[(1R)-3-amino-1-hydroxypropyl]-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]-10,12-dimethyltetradecanamide
  参考文献：
  名称：

  Process for preparation of Caspofungin acetate

  摘要：

  制备卡泊芬凝胶乙酸酯的过程包括以下步骤： A. 选择性脱水肺炎链霉素Bo以获得一个腈； B. 还原腈为一级胺； C. 在适当的溶剂中将一级胺与芳基硫醇反应以获得硫醚； D. 将硫醚与乙二胺反应以获得具有以下式的卡泊芬凝胶乙酸酯：

  公开号：

  US20100168415A1

文献信息

• Process for preparing pharmaceutical compound and intermediates thereof
  申请人：Heggelund Audun

  公开号：US20090312541A1

  公开（公告）日：2009-12-17

  The present invention relates to novel intermediates of formula VII, or an acid addition salt or a solvate thereof, wherein R 1 is —(CO)NH 2 , —CH 2 NH 2 or —CN; R 2 ═R 3 ═H or R 2 and R 3 together form a cyclic boronate or borate ester; X is a helping group selected from the group consisting of i) a five or six membered heterocyclic aromatic ring and derivatives thereof comprising at least one N-atom being a part of an imine-group, wherein said N-atom forms the point of connection to the cyclohexapeptide ring, and ii) tetrazolyl and derivatives thereof for which a nitrogen atom forms the point of connection to the cyclohexapeptide ring, and a process for the preparation of caspofungin utilizing said intermediates.

  本发明涉及公式VII的新型中间体，或其酸盐或溶剂结晶体，其中R1为—(CO)NH2，—CH2NH2或—CN；R2=R3=H或R2和R3一起形成环状硼酸酯或硼酸酯；X是从i)五元或六元杂环芳香环及其衍生物中选择的辅助基团，其中至少有一个N原子是亚胺基的一部分，其中所述N原子形成连接到环己肽环的连接点，以及ii)四唑基及其衍生物，其中氮原子形成连接到环己肽环的连接点，并利用这些中间体制备卡泊霉素的方法。
• US8048853B2
  申请人：——

  公开号：US8048853B2

  公开（公告）日：2011-11-01
• [EN] COMPOSITIONS AND METHODS FOR THE TREATMENT OF FUNGAL INFECTIONS<br/>[FR] COMPOSITIONS ET MÉTHODES POUR LE TRAITEMENT D'INFECTIONS FONGIQUES
  申请人：CIDARA THERAPEUTICS INC

  公开号：WO2015035102A2

  公开（公告）日：2015-03-12

  Compositions and methods for the treatment of fungal infections including compounds containing a pathogen pattern recognition receptor ligand and a β 1,3-glucan synthase inhibitor are disclosed. In particular, compounds containing a lipopeptide moiety and a formyl peptide receptor ligand can be used in the treatment of fungal infections caused by a fungus of the genus Aspergillus or Candida.
• Process for preparation of Caspofungin acetate
  申请人：Lee Kwang-Chung

  公开号：US20100168415A1

  公开（公告）日：2010-07-01

  A process for making caspofungin acetate comprising the steps of: A. selectively dehydrating pneumocandin Bo to obtain a nitrile; B. reducing the nitrile to primary amine; C. reacting the primary amine with an arylthiol in a suitable solvent to obtain a thioether; and D. reacting the thioether with ethylenediamine to obtain the caspofungin acetate having a formula as shown below:

  制备卡泊芬凝胶乙酸酯的过程包括以下步骤： A. 选择性脱水肺炎链霉素Bo以获得一个腈； B. 还原腈为一级胺； C. 在适当的溶剂中将一级胺与芳基硫醇反应以获得硫醚； D. 将硫醚与乙二胺反应以获得具有以下式的卡泊芬凝胶乙酸酯：
• Synthesis of the Antifungal β-1,3-Glucan Synthase Inhibitor CANCIDAS (Caspofungin Acetate) from Pneumocandin B₀
  作者：William R. Leonard,、Kevin M. Belyk、David A. Conlon、Dean R. Bender、Lisa M. DiMichele、Ji Liu、David L. Hughes

  DOI：10.1021/jo062008i

  日期：2007.3.1

  A novel three-step synthesis of the highly functionalized antifungal agent CANCIDAS (caspofungin acetate, 2) is described, starting from the natural product pneumocandin B-0 (1). The highlights of the synthesis include a stereoselective formation of a phenylthioaminal, a remarkable chemoselective, high-yielding, one-step borane reduction of a primary amide, and a stereoselective substitution of the phenylthioaminal with ethylenediamine producing 2 in a 45% overall yield.