(R)-2-((R)-1-(tert-butyldimethylsilanyloxy)-12-{(1R,2S)-2-[14-((1R,2S)-2-eicosylcyclopropyl)tetradecyl]cyclopropyl}dodecyl)hexacosanoic acid | 1236137-05-5

• 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-(tert-butyldimethylsilanyloxy)-12-{(1R,2S)-2-[14-((1R,2S)-2-eicosylcyclopropyl)tetradecyl]cyclopropyl}dodecyl)hexacosanoic acid
• 英文别名: (R)-2-((R)-1-(tert-butyl-dimethyl-silanyloxy)-12-{(1R,2S)-2-[14-((1R,2S)-2-icosyl-cyclopropyl)-tetradecyl]-cyclopropyl}-dodecyl)-hexacosanoic acid
• CAS: 1236137-05-5
• 化学式: C₈₄H₁₆₆O₃Si
• 分子量: 1252.33
• InChiKey: VKWBVXHHBNQCOI-YXEQRGHYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  30.53
• 重原子数：
  88.0
• 可旋转键数：
  73.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.99
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2,3,4,2',3',4'-hexakis-O-(trimethylsilyl)-α,α-trehalose 、 (R)-2-((R)-1-(tert-butyldimethylsilanyloxy)-12-{(1R,2S)-2-[14-((1R,2S)-2-eicosylcyclopropyl)tetradecyl]cyclopropyl}dodecyl)hexacosanoic acid 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 144.0h， 生成 2,3,4-tri-O-trimethylsilyl-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)-2,3,4-tri-O-trimethylsilyl-α-D-glucopyranoside 、 R,2S,3S,4R,5S)-5-((R)-4-((S)-16-((1R,2S)-2-(14-((1R,2S)-2-icosylcyclopropyl)tetradecyl)cyclopropyl)-2,2,3,3-tetramethylhexadecan-5-yl)-3-methyleneoctacosyl)-2,3,4-trineopentylcyclohexyl)methane
  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
• 作为产物：
  描述：

  在 水 、 potassium carbonate 、 potassium hydrogensulfate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 (R)-2-((R)-1-(tert-butyldimethylsilanyloxy)-12-{(1R,2S)-2-[14-((1R,2S)-2-eicosylcyclopropyl)tetradecyl]cyclopropyl}dodecyl)hexacosanoic acid
  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

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。
• 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.