5-(7-[(1S,2R)-2-((17R,18R)-17-methoxy-18-methylhexatriacontyl)cyclopropyl]heptylsulfonyl)-1-phenyl-1H-tetrazole | 934503-25-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(7-[(1S,2R)-2-((17R,18R)-17-methoxy-18-methylhexatriacontyl)cyclopropyl]heptylsulfonyl)-1-phenyl-1H-tetrazole
• CAS: 934503-25-0
• 化学式: C₅₅H₁₀₀N₄O₃S
• 分子量: 897.49
• InChiKey: YFOCGPBBZZQKNP-KBFWZXMYSA-N

物化性质

• 沸点：
  868.5±57.0 °C(predicted)
• 密度：
  1.02±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  16.96
• 重原子数：
  63.0
• 可旋转键数：
  46.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  86.97
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  5-(7-[(1S,2R)-2-((17R,18R)-17-methoxy-18-methylhexatriacontyl)cyclopropyl]heptylsulfonyl)-1-phenyl-1H-tetrazole 在 potassium diazodicarboxylate 、 溶剂黄146 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.0h， 生成 (R)-2-{(R)-1-acetoxy-18-[(1S,2R)-2-((17R,18R)-17-methoxy-18-methylhexatriacontyl)cyclopropyl]-octadecyl}hexacosanoic acid methyl ester
  参考文献：
  名称：

  The first syntheses of single enantiomers of the major methoxymycolic acid of Mycobacterium tuberculosis

  摘要：

  The synthesis of three stereoisomers of a major homologue of the methoxymycolic acids present in Mycobacterium tuberculosis is described. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.01.007
• 作为产物：
  描述：

  2,2-dimethyl-propionic acid 8-bromooctyl ester 在 palladium on activated charcoal 氢氧化钾 、 N-溴代丁二酰亚胺(NBS) 、 ammonium heptamolybdate 、 ammonium molybdate tetrahydrate 、 2,4,6-triisopropyl sulfonylhydrazide 、 氢气 、 双氧水 、 potassium carbonate 、 三苯基膦 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 81.0h， 生成 5-(7-[(1S,2R)-2-((17R,18R)-17-methoxy-18-methylhexatriacontyl)cyclopropyl]heptylsulfonyl)-1-phenyl-1H-tetrazole
  参考文献：
  名称：

  The first syntheses of single enantiomers of the major methoxymycolic acid of Mycobacterium tuberculosis

  摘要：

  The synthesis of three stereoisomers of a major homologue of the methoxymycolic acids present in Mycobacterium tuberculosis is described. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.01.007

文献信息

• Thiol modified mycolic acids
  作者：Mohammed O. Balogun、Enlli H. Huws、Muthana M. Sirhan、Ahmed D. Saleh、Juma’a R. Al Dulayymi、Lynne Pilcher、Jan A. Verschoor、Mark S. Baird

  DOI：10.1016/j.chemphyslip.2013.03.004

  日期：2013.7

  Patient serum antibodies to mycolic acids have the potential to be surrogate markers of active tuberculosis (TB) when they can be distinguished from the ubiquitously present cross-reactive antibodies to cholesterol. Mycolic acids are known to interact more strongly with antibodies present in the serum of patients with active TB than in patients with latent TB or no TB. Examples of single stereoisomers of mycolic acids with chain lengths corresponding to major homologues of those present in Mycobacterium tuberculosis have now been synthesised with a sulfur substituent on the terminal position of the alpha-chain; initial studies have established that one of these binds to a gold electrode surface, offering the potential to develop second generation sensors for diagnostic patient antibody detection. (c) 2013 Elsevier Ireland Ltd. All rights reserved.