methyl (R)-2-[(R)-1-(tert-butyldimethylsilanyloxy)-3-oxopropyl]tetracosanoate | 1204202-13-0

• 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: methyl (R)-2-[(R)-1-(tert-butyldimethylsilanyloxy)-3-oxopropyl]tetracosanoate
• 英文别名: (R)-2-[(R)-1-(tert-butyldimethylsilanyloxy)-3-hydroxypropyl]tetracosanoic acid methyl ester；methyl (2R)-2-[(1R)-1-[tert-butyl(dimethyl)silyl]oxy-3-oxopropyl]tetracosanoate
• CAS: 1204202-13-0
• 化学式: C₃₄H₆₈O₄Si
• 分子量: 568.997
• InChiKey: CLVYVPDEFXEVNM-ROJLCIKYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.97
• 重原子数：
  39
• 可旋转键数：
  29
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (R)-2-[(R)-1-(tert-butyldimethylsilanyloxy)-3-oxopropyl]tetracosanoate 、 5-[(R)-18-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)nonadecane sulfonyl]-1-phenyl-1H-tetrazole 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 以89%的产率得到methyl (E/Z)-(2R,3R,23R)-3-(tert-butyldimethylsilanyloxy)-23-((S)-2,2-dimethyl[1.3]dioxolan-4-yl)-2-docosyltetracos-5-enoate
  参考文献：
  名称：

  The first synthesis of epoxy-mycolic acids

  摘要：

  We report the synthesis of single enantiomers of two epoxy-mycolic acids containing an alpha-methyl-trans-alkene. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.01.078
• 作为产物：
  描述：

  (R)-2-[(R)-1-(tert-butyldimethylsilanyloxy)-3-hydroxypropyl]tetracosanoic acid methyl ester 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以96%的产率得到methyl (R)-2-[(R)-1-(tert-butyldimethylsilanyloxy)-3-oxopropyl]tetracosanoate
  参考文献：
  名称：

  The synthesis of a major α′-mycolic acid of Mycobacterium smegmatis

  摘要：

  The synthesis of (2R,3R,Z)-2-docosyl-3-hydroxytetracont-21-enoic acid, a significant alpha'-mycolic acid of Mycobacterium smegmatis and other mycobacteria is reported. (C) 2010 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.chemphyslip.2010.05.203

文献信息

• The synthesis of single enantiomers of trans-alkene containing mycolic acids and related sugar esters
  作者：Hanan M. Ali、Gani Koza、Rwoa'a T. Hameed、Richard Rowles、Carys Davies、Juma'a R. Al Dulayymi、Christopher D. Gwenin、Mark S. Baird

  DOI：10.1016/j.tet.2016.08.089

  日期：2016.11

  Routes to single enantiomers of hydroxy, methoxy and ketomycolic acids containing an α-methyl-trans-alkene unit as well as related trehalose, glucose, arabinose and glycerol esters are described. In serodiagnostic assays to detect antibodies to mycobacterial lipids, the trehalose esters give higher responses to the serum of patients with culture positive tuberculosis than to that of culture negative

  描述了含有α-甲基-反式-链烯烃单元的羟基，甲氧基和酮麦考酸的单一对映体以及相关的海藻糖，葡萄糖，阿拉伯糖和甘油酯的途径。在检测抗分枝杆菌脂质抗体的血清诊断测定中，海藻糖酯对培养阳性结核病患者的血清反应比对培养阴性结核病患者的反应高。
• The synthesis of single enantiomers of trans-alkene-containing mycolic acids
  作者：Gani Koza、Richard Rowles、Cornelia Theunissen、Juma’a R. Al-Dulayymi、Mark S. Baird

  DOI：10.1016/j.tetlet.2009.10.009

  日期：2009.12

  We report routes to single enantiomers of hydroxy and ketomycolic acids containing an α-methyl-trans-alkene unit.

  我们报道了含有α-甲基-反式-烯烃单元的羟基和酮麦考酸的单一对映体的路线。
• Synthetic epoxy-mycolic acids
  作者：Dakhil Z. Al Kremawi、Juma'a R. Al Dulayymi、Mark S. Baird

  DOI：10.1016/j.tet.2014.06.089

  日期：2014.10

  We report the synthesis of single enantiomers of epoxy-mycolic acids containing an alpha-methyl-transalkene or a cis-cyclopropane with structures that match those of major isomers of such molecules present in complex mixtures in Mycobacteria such as Mycobacterium fortuitum or Mycobacterium smegmatis (C) 2014 Elsevier Ltd. All rights reserved.
• The synthesis of a major α′-mycolic acid of Mycobacterium smegmatis
  作者：Maged Muzael、Gani Koza、Juma’a J. Al Dulayymi、Mark S. Baird

  DOI：10.1016/j.chemphyslip.2010.05.203

  日期：2010.9

  The synthesis of (2R,3R,Z)-2-docosyl-3-hydroxytetracont-21-enoic acid, a significant alpha'-mycolic acid of Mycobacterium smegmatis and other mycobacteria is reported. (C) 2010 Elsevier Ireland Ltd. All rights reserved.
• The first synthesis of epoxy-mycolic acids
  作者：Dakhil Z. Al Kremawi、Juma’a R. Al Dulayymi、Mark S. Baird

  DOI：10.1016/j.tetlet.2010.01.078

  日期：2010.3

  We report the synthesis of single enantiomers of two epoxy-mycolic acids containing an alpha-methyl-trans-alkene. (C) 2010 Elsevier Ltd. All rights reserved.