(R)-2-{(R)-17-[(1S,2R)-2-((1S,21S)-1,21-dimethyl-20-oxononatriacontyl)cyclopropyl]-1-hydroxyheptadecyl} hexacosanoic acid | 1446326-57-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (R)-2-{(R)-17-[(1S,2R)-2-((1S,21S)-1,21-dimethyl-20-oxononatriacontyl)cyclopropyl]-1-hydroxyheptadecyl} hexacosanoic acid
• 英文别名: (R)-2-{(R)-1-(tert-dutyldimethylsilanyloxy)-17-[(1S,2R)-2-((1S,20S,21S)-20-hydroxy-1,21-dimethylnonatriacontyl)cyclopropyl]heptadecyl}hexacosanoic acid；(2R)-2-[(1R)-1-hydroxy-17-[(1S,2R)-2-[(2S,22S)-22-methyl-21-oxotetracontan-2-yl]cyclopropyl]heptadecyl]hexacosanoic acid
• CAS: 1446326-57-3
• 化学式: C₈₇H₁₇₀O₄
• 分子量: 1280.3
• InChiKey: DVNAMZNTINAEPO-XYOVMDIOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  40.6
• 重原子数：
  91
• 可旋转键数：
  80
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.98
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-2-{(R)-17-[(1S,2R)-2-((1S,21S)-1,21-dimethyl-20-oxononatriacontyl)cyclopropyl]-1-hydroxyheptadecyl} hexacosanoic acid 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以88%的产率得到(R)-2-{(R)-17-[(1S,2R)-2-((1S,21S)-1,21-dimethyl-20-oxononatriacontyl)cyclopropyl]-1-(tert-butyldimethylsilanyloxy)heptadecyl}hexacosanoic acid
  参考文献：
  名称：

  Synthetic trehalose di- and mono-esters of α-, methoxy- and keto-mycolic acids

  摘要：

  Synthetic mycolic acids matching the overall structure of the major mycolic acids of Mycobacterium tuberculosis are coupled to trehalose to generate the corresponding synthetic trehalose monomycolate (TMM) and trehalose dimycolate (TDM; cord factor), either with two identical or two different mycolic acids. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.10.072
• 作为产物：
  描述：

  (R)-2-{(R)-17-[(1S,2R)-2-((1S,21S)-1,21-dimethyl-20-oxononatriacontyl)cyclopropyl]-1-(tert-butyldimethylsilanyloxy)heptadecyl}hexacosanoic acid 在 吡啶 、 pyridine hydrofluoride 作用下， 以 四氢呋喃 为溶剂， 反应 17.0h， 以84%的产率得到(R)-2-{(R)-17-[(1S,2R)-2-((1S,21S)-1,21-dimethyl-20-oxononatriacontyl)cyclopropyl]-1-hydroxyheptadecyl} hexacosanoic acid
  参考文献：
  名称：

  The synthesis of methoxy and keto mycolic acids containing methyl-trans-cyclopropanes

  摘要：

  The syntheses of a number of methoxy and keto-mycolic acids containing an alpha-methyl-trans-cyclopropane unit and with chain lengths identical to those reported in major homologues in natural samples are reported. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.04.134

文献信息

• The synthesis of methoxy and keto mycolic acids containing methyl-trans-cyclopropanes
  作者：Gani Koza、Maged Muzael、Richard R. Schubert-Rowles、Cornelia Theunissen、Juma'a R. Al Dulayymi、Mark S. Baird

  DOI：10.1016/j.tet.2013.04.134

  日期：2013.7

  The syntheses of a number of methoxy and keto-mycolic acids containing an alpha-methyl-trans-cyclopropane unit and with chain lengths identical to those reported in major homologues in natural samples are reported. (C) 2013 Elsevier Ltd. All rights reserved.
• Synthetic trehalose di- and mono-esters of α-, methoxy- and keto-mycolic acids
  作者：Juma'a R. Al Dulayymi、Mark S. Baird、Maximiliano Maza-Iglesias、Rwoa'a T. Hameed、Klarah S. Baols、Majed Muzael、Ahmed D. Saleh

  DOI：10.1016/j.tet.2014.10.072

  日期：2014.12

  Synthetic mycolic acids matching the overall structure of the major mycolic acids of Mycobacterium tuberculosis are coupled to trehalose to generate the corresponding synthetic trehalose monomycolate (TMM) and trehalose dimycolate (TDM; cord factor), either with two identical or two different mycolic acids. (C) 2014 Elsevier Ltd. All rights reserved.