1-benzoxy-(3R,7R,11S,15S)-3,711,15-tetramethyl-4-(E/Z)-8-(E/Z)-decosa-4,8-diene | 1443233-10-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 1-benzoxy-(3R,7R,11S,15S)-3,711,15-tetramethyl-4-(E/Z)-8-(E/Z)-decosa-4,8-diene
• CAS: 1443233-10-0
• 化学式: C₃₃H₅₆O
• 分子量: 468.807
• InChiKey: VFNFHBMZGFMJHW-YDPTYEFTSA-N

反应信息

• 作为产物：
  描述：

  8-benzoxy-(2R,6R)-2,6-dimethyl-4-(Z/E)-4-octenol-1 在 戴斯-马丁氧化剂 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 1-benzoxy-(3R,7R,11S,15S)-3,711,15-tetramethyl-4-(E/Z)-8-(E/Z)-decosa-4,8-diene 、 1-benzoxy-(3R,7R,11R,15S)-3,711,15-tetramethyl-4-(E/Z)-8-(E/Z)-decosa-4,8-diene
  参考文献：
  名称：

  Highly Stereocontrolled Total Synthesis of β-d-Mannosyl Phosphomycoketide: A Natural Product from Mycobacterium tuberculosis

  摘要：

  beta-D-Mannosyl phosphomycoketide (C-32-MPM), a naturally occurring glycolipid found in the cell walls of Mycobacterium tuberculosis, acts as a potent antigen to activate T-cells upon presentation by CD1c protein. The lipid portion of C-32-MPM contains, a C-32-mycoketide, consisting of a saturated oligoisoprenoid chain with five chiral methyl branches. Here we develop several stereocontrolled approaches to assemble the oligoisoprenoid chain with high stereopurity (>96%) using Julia-Kocienski olefinations followed by diimide reduction. By careful choice of olefination sites, we could derive all chirality from a single commercial compound, methyl (2S)-3-hydroxy-2-methylpropionate (>99% ee). Our approach is the first highly stereocontrolled method to prepare C-32-MPM molecule with >96% stereopurity from a single >99% ee starting material. We anticipate that our methods will facilitate the highly stereocontrolled synthesis of a variety of other natural products containing chiral oligoisoprenoid-like chains, including vitamins, phytol, insect pheromones, and archaeal lipids.

  DOI：

  10.1021/jo4006602