(R)-2-{(R)-17-[(1S,2R)-2-((1S,21S)-1,21-dimethyl-20-oxononatriacontyl)cyclopropyl]-1-(tert-butyldimethylsilanyloxy)heptadecyl}hexacosanoic acid | 1446326-73-3

• 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-(tert-butyldimethylsilanyloxy)heptadecyl}hexacosanoic acid
• CAS: 1446326-73-3
• 化学式: C₉₃H₁₈₄O₄Si
• 分子量: 1394.57
• InChiKey: CIOLIOYCJRKRRR-HQTINYDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  33.46
• 重原子数：
  98.0
• 可旋转键数：
  82.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.98
• 拓扑面积：
  63.6
• 氢给体数：
  1.0
• 氢受体数：
  3.0

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-(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
• 作为产物：
  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

文献信息

• The synthesis of mycobacterial dimycoloyl diarabinoglycerol based on defined synthetic mycolic acids
  作者：Omar T. Ali、Mohsin O. Mohammed、Paul J. Gates、Mark S. Baird、Juma’a R. Al Dulayymi

  DOI：10.1016/j.chemphyslip.2019.01.002

  日期：2019.7

  and potentially valuable antigens in the serodiagnosis of mycobacterial infections. We now report the highly stereocontrolled synthesis of diacyl l-glycerol-(1'→1)-β-d-arabinofuranosyl-α-d-arabinofuranosides based on simple fatty acids and single defined synthetic mycolic acids. NMR analysis confirmed that the synthetic core was identical to that in natural mixtures.

  从分枝杆菌中分离出来的天然二甲酰氯二氮杂甘油的复杂混合物在分枝杆菌感染的血清学诊断中既是有效的免疫信号传导剂，又是潜在有价值的抗原。现在，我们报告基于简单脂肪酸和单一定义的合成霉菌酸，对二酰基L-甘油-（1'→1）-β-d-阿拉伯呋喃糖基-α-d-阿拉伯呋喃糖苷进行高度立体控制的合成。NMR分析证实合成核与天然混合物中的核相同。