1-deoxy-1-[(2'S,3'S,4'R)-2'-azido-3',4'-dihydroxyoctadec-5'-ynyl]-2,3,4,6-tetra-O-benzyl-α-D-galactopyranose | 949570-34-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-deoxy-1-[(2'S,3'S,4'R)-2'-azido-3',4'-dihydroxyoctadec-5'-ynyl]-2,3,4,6-tetra-O-benzyl-α-D-galactopyranose
• CAS: 949570-34-7
• 化学式: C₅₂H₆₇N₃O₇
• 分子量: 846.12
• InChiKey: ZSKNISSYBFTXND-MJJUNOJKSA-N

反应信息

• 作为反应物：
  描述：

  1-deoxy-1-[(2'S,3'S,4'R)-2'-azido-3',4'-dihydroxyoctadec-5'-ynyl]-2,3,4,6-tetra-O-benzyl-α-D-galactopyranose 在 吡啶 作用下， 以 甲苯 为溶剂， 生成 [(4R,5S,6S)-4-acetyloxy-3-dodecyl-6-[[(2R,3S,4R,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]methyl]-5,6-dihydro-4H-pyrrolo[1,2-c]triazol-5-yl] acetate
  参考文献：
  名称：

  Total Synthesis of α-1C-Galactosylceramide, an Immunostimulatory C-Glycosphingolipid, and Confirmation of the Stereochemistry in the First-Generation Synthesis

  摘要：

  A nonisosteric alpha-C-glycoside analogue of KRN7000 (alpha-1C-GalCer, 1) was reported to induce a selective type of cytokine release in human invariant natural killer cells in vitro. We report here a very concise synthetic route to 1 and its analogue 1'. The key steps include olefin cross-metathesis, Sharpless asymmetric epoxidation, and epoxide opening by NaN3/NH4Cl. Inversion of configuration at the amide-bearing carbon in the phytosphingosine backbone constructed by epoxide opening in our previous synthesis of 1 was verified, indicating that remote group participation is not involved during the epoxide-opening reaction.

  DOI：

  10.1021/jo201450s
• 作为产物：
  描述：

  在 sodium azide 、 水 、 氯化铵 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以63%的产率得到1-deoxy-1-[(2'S,3'S,4'R)-2'-azido-3',4'-dihydroxyoctadec-5'-ynyl]-2,3,4,6-tetra-O-benzyl-α-D-galactopyranose
  参考文献：
  名称：

  Total Synthesis of α-1C-Galactosylceramide, an Immunostimulatory C-Glycosphingolipid, and Confirmation of the Stereochemistry in the First-Generation Synthesis

  摘要：

  A nonisosteric alpha-C-glycoside analogue of KRN7000 (alpha-1C-GalCer, 1) was reported to induce a selective type of cytokine release in human invariant natural killer cells in vitro. We report here a very concise synthetic route to 1 and its analogue 1'. The key steps include olefin cross-metathesis, Sharpless asymmetric epoxidation, and epoxide opening by NaN3/NH4Cl. Inversion of configuration at the amide-bearing carbon in the phytosphingosine backbone constructed by epoxide opening in our previous synthesis of 1 was verified, indicating that remote group participation is not involved during the epoxide-opening reaction.

  DOI：

  10.1021/jo201450s