(R)-2-((R)-1-hydroxy-12-{(1R,2S)-2-[14-((1R,2S)-2-eicosylcyclopropyl)tetradecyl]cyclopropyl}dodecyl)hexacosanoic acid | 1170667-19-2

• 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)-1-hydroxy-12-{(1R,2S)-2-[14-((1R,2S)-2-eicosylcyclopropyl)tetradecyl]cyclopropyl}dodecyl)hexacosanoic acid
• 英文别名: (2R)-2-{(1R)-1-hydroxy-12-[(1R,2S)-2-[14-[(1R,2S)-2-eicosylcyclopropyl]tetradecyl]cyclopropyl]dodecyl}hexacosanoic acid；(R)-2-((R)-1-hydroxy-12-{(1R,2S)-2-[14-((1R,2S)-2-icosyl-cyclopropyl)-tetradecyl]-cyclopropyl}-dodecyl)-hexacosanoic acid；(2R)-2-{(1R)-1-hydroxy-12-[(1R,2S)-2-{14-[(1R,2S)-2-icosylcyclopropyl]tetradecyl}cyclopropyl]dodecyl}hexacosanoic acid；(2R)-2-[(1R)-1-hydroxy-12-[(1R,2S)-2-[14-[(1R,2S)-2-icosylcyclopropyl]tetradecyl]cyclopropyl]dodecyl]hexacosanoic acid
• CAS: 1170667-19-2
• 化学式: C₇₈H₁₅₂O₃
• 分子量: 1138.06
• InChiKey: UJPOZISPJYFURI-BWMTUFAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  37.6
• 重原子数：
  81
• 可旋转键数：
  71
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.99
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-2-((R)-1-hydroxy-12-{(1R,2S)-2-[14-((1R,2S)-2-eicosylcyclopropyl)tetradecyl]cyclopropyl}dodecyl)hexacosanoic acid 在 盐酸 、 cesium bicarbonate 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 35.0h， 生成 (R)-2,3-dihydroxypropyl (R)-2-((R)-1-hydroxy-12-((1R,2S)-2-(14-((1R,2S)-2-eicosyl-cyclopropyl)tetradecyl)cyclopropyl)dodecyl)hexacosanoate
  参考文献：
  名称：

  来自合成霉菌酸的甘油霉菌酸酯。

  摘要：

  描述了衍生自单一合成α-，酮-和甲氧基-霉菌酸的R-和S-甘油霉菌酸酯。

  DOI：

  10.1016/j.carres.2017.04.023

文献信息

• Preparation of the tri-arabino di-mycolate fragment of mycobacterial arabinogalactan from defined synthetic mycolic acids
  作者：Mohsin O. Mohammed、Juma'a R. Al Dulayymi、Mark S. Baird

  DOI：10.1016/j.carres.2016.11.006

  日期：2017.1

  An efficient synthetic approach to tri-arabino di-mycolates, using structurally defined synthetic alpha-, keto and methoxy mycolic acids is described.

  描述了一种有效的合成方法，使用结构上定义的合成α-，酮和甲氧基霉菌酸合成三阿拉伯糖基二霉菌酸酯。
• METHOD AND COMPOSITIONS
  申请人：Baird Mark Stephen

  公开号：US20120045478A1

  公开（公告）日：2012-02-23

  A method of preparing a compound of formula (III): wherein x is from 1 to 6, y is from 1 to 12, z is from 0 to 10, each M and each M′ is independently a mycolic acid residue including a β-hydroxy acid moiety and each S is a monosaccharide unit; the method comprising reacting one or more mycolic acids with one or more saccharide units wherein the hydroxyl group of each β-hydroxy acid moiety is protected prior to reaction with the one or more saccharide units.

  一种制备式（III）化合物的方法：其中x为1至6，y为1至12，z为0至10，每个M和每个M′都是独立的包括β-羟基酸基团的肉豆蔻酸残基，每个S是单糖单元；该方法包括将一个或多个肉豆蔻酸与一个或多个单糖单元反应，其中每个β-羟基酸基团的羟基在与一个或多个单糖单元反应之前被保护。
• Glucose monomycolates based on single synthetic mycolic acids
  作者：Mohaned M. Sahb、Juma’a R. Al Dulayymi、Mark S. Baird

  DOI：10.1016/j.chemphyslip.2015.06.005

  日期：2015.9

  The preparation of 6-O-mycolylglucoses (GMMs) from single synthetic mycolic acids matching the overall structure of some of the major natural glucose monomycolates of Mycobacterium tuberculosis and other mycobacteria is reported. (C) 2015 Elsevier Ireland 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.
• The first unique synthetic mycobacterial cord factors
  作者：Juma’a R. Al Dulayymi、Mark S. Baird、Maximiliano Maza-Iglesias、Seppe Vander Beken、Johan Grooten

  DOI：10.1016/j.tetlet.2009.03.213

  日期：2009.7

  Synthetic mycolic acids matching the overall structure of the major alpha- and methoxy-mycolic acids of Mycobacterium tuberculosis are coupled to trehalose to generate the corresponding synthetic trehalose dimycolate (TDM; cord factor) and trehalose monomycolate (TMM). (C) 2009 Elsevier Ltd. All rights reserved.