6-O-[(R)-2-((R)-1-((tert-butyldimethylsilyl)oxy)-18-((1R,2S)-2-((17S,18S)-17-methoxy-18-methylhexatriacontyl)cyclopropyl)octadecyl)hexacosanoyl]-α-D-glucopyranosyl-(1→1)-α-D-glucopyranoside | 1170667-16-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: 6-O-[(R)-2-((R)-1-((tert-butyldimethylsilyl)oxy)-18-((1R,2S)-2-((17S,18S)-17-methoxy-18-methylhexatriacontyl)cyclopropyl)octadecyl)hexacosanoyl]-α-D-glucopyranosyl-(1→1)-α-D-glucopyranoside
• 英文别名: [(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl (2R)-2-[(1R)-1-[tert-butyl(dimethyl)silyl]oxy-18-[(1R,2S)-2-[(17S,18S)-17-methoxy-18-methylhexatriacontyl]cyclopropyl]octadecyl]hexacosanoate
• CAS: 1170667-16-9
• 化学式: C₁₀₃H₂₀₂O₁₄Si
• 分子量: 1692.81
• InChiKey: CBEUERJJSILTQL-JLIOJWIBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  27.96
• 重原子数：
  118
• 可旋转键数：
  88
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.99
• 拓扑面积：
  214
• 氢给体数：
  7
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  6-O-[(R)-2-((R)-1-((tert-butyldimethylsilyl)oxy)-18-((1R,2S)-2-((17S,18S)-17-methoxy-18-methylhexatriacontyl)cyclopropyl)octadecyl)hexacosanoyl]-α-D-glucopyranosyl-(1→1)-α-D-glucopyranoside 在 pyridine hydrofluoride 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 17.0h， 以78%的产率得到6-O-[(R)-2-((R)-1-hydroxy-18-((1R,2S)-2-((17S,18S)-17-methoxy-18-methylhexatriacontyl)cyclopropyl)octadecyl)hexacosanoyl]-α-D-glucopyranosyl-(1→1)-α-D-glucopyranoside
  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：

  2,3,4-tri-O-trimethylsilyl-6-O-[(R)-2-((R)-1-((tert-butyldimethylsilyl)oxy)-18-((1R,2S)-2-((17S,18S)-17-methoxy-18-methylhexatriacontyl)cyclopropyl)octadecyl)hexacosanoyl]-α-D-glucopyranosyl-(1→1)-2,3,4-tri-O-trimethylsilyl-α-D-glucopyranoside 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以80%的产率得到6-O-[(R)-2-((R)-1-((tert-butyldimethylsilyl)oxy)-18-((1R,2S)-2-((17S,18S)-17-methoxy-18-methylhexatriacontyl)cyclopropyl)octadecyl)hexacosanoyl]-α-D-glucopyranosyl-(1→1)-α-D-glucopyranoside
  参考文献：
  名称：

  The first unique synthetic mycobacterial cord factors

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2009.03.213