6-O-[(R)-2-((R)-1-hydroxy-12-{(1R,2S)-2-[14-((1R,2S)-2-eicosylcyclopropyl)tetradecyl]cyclopropyl}dodecyl)hexacosanoyl]-α-D-glucopyranosyl-(1→1)-6'-O-[(R)-2-((R)-1-hydroxy-12-{(1R,2S)-2-[14-((1R,2S)-2-eicosylcyclopropyl)tetradecyl]cyclopropyl}dodecyl)hexacosanoyl]-α-D-glucopyranoside | 1170667-21-6

• 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-hydroxy-12-{(1R,2S)-2-[14-((1R,2S)-2-eicosylcyclopropyl)tetradecyl]cyclopropyl}dodecyl)hexacosanoyl]-α-D-glucopyranosyl-(1→1)-6'-O-[(R)-2-((R)-1-hydroxy-12-{(1R,2S)-2-[14-((1R,2S)-2-eicosylcyclopropyl)tetradecyl]cyclopropyl}dodecyl)hexacosanoyl]-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-[[(2R)-2-[(1R)-1-hydroxy-12-[(1R,2S)-2-[14-[(1R,2S)-2-icosylcyclopropyl]tetradecyl]cyclopropyl]dodecyl]hexacosanoyl]oxymethyl]oxan-2-yl]oxyoxan-2-yl]methyl (2R)-2-[(1R)-1-hydroxy-12-[(1R,2S)-2-[14-[(1R,2S)-2-icosylcyclopropyl]tetradecyl]cyclopropyl]dodecyl]hexacosanoate
• CAS: 1170667-21-6
• 化学式: C₁₆₈H₃₂₂O₁₅
• 分子量: 2582.4
• InChiKey: CWJJNIFYBIOGTB-NHXGMYBRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  71.5
• 重原子数：
  183
• 可旋转键数：
  150
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.99
• 拓扑面积：
  242
• 氢给体数：
  8
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  6-O-[(R)-2-((R)-1-(tert-butyldimethylsilanyloxy)-12-{(1R,2S)-2-[14-((1R,2S)-2-eicosylcyclopropyl)tetradecyl]cyclopropyl}dodecyl)hexacosanoyl]-α-D-glucopyranosyl-(1→1)-6'-O-[(R)-2-((R)-1-(tert-butyldimethylsilanyloxy)-12-{(1R,2S)-2-[14-((1R,2S)-2-eicosylcyclopropyl)tetradecyl]cyclopropyl}dodecyl)hexacosanoyl]-α-D-glucopyranoside 在 吡啶 、 氟化氢吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 17.0h， 以54%的产率得到6-O-[(R)-2-((R)-1-hydroxy-12-{(1R,2S)-2-[14-((1R,2S)-2-eicosylcyclopropyl)tetradecyl]cyclopropyl}dodecyl)hexacosanoyl]-α-D-glucopyranosyl-(1→1)-6'-O-[(R)-2-((R)-1-hydroxy-12-{(1R,2S)-2-[14-((1R,2S)-2-eicosylcyclopropyl)tetradecyl]cyclopropyl}dodecyl)hexacosanoyl]-α-D-glucopyranoside
  参考文献：
  名称：

  METHOD AND COMPOSITIONS

  摘要：

  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。

  公开号：

  US20120045478A1

文献信息

• 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。
• 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.
• 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.