(2S,3R,4E)-[2',3',6'-tri-O-benzoyl-4'-O-(2'',3'',4'',6''-tetra-O-benzoyl-β-D-galactopyranosyl)-β-D-glucopyranosyl]-(1'->1)-2-(hexadecanoylamido)-3-O-benzoyl-4-octadecene-1,3-diol | 167871-75-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 鞘脂
• 英文名称: (2S,3R,4E)-[2',3',6'-tri-O-benzoyl-4'-O-(2'',3'',4'',6''-tetra-O-benzoyl-β-D-galactopyranosyl)-β-D-glucopyranosyl]-(1'->1)-2-(hexadecanoylamido)-3-O-benzoyl-4-octadecene-1,3-diol
• CAS: 167871-75-2
• 化学式: C₁₀₂H₁₁₉NO₂₁
• 分子量: 1695.06
• InChiKey: SSUWNBPEFINBQN-SYUQCHCASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  20.13
• 重原子数：
  124.0
• 可旋转键数：
  52.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  276.42
• 氢给体数：
  1.0
• 氢受体数：
  21.0

反应信息

• 作为反应物：
  描述：

  (2S,3R,4E)-[2',3',6'-tri-O-benzoyl-4'-O-(2'',3'',4'',6''-tetra-O-benzoyl-β-D-galactopyranosyl)-β-D-glucopyranosyl]-(1'->1)-2-(hexadecanoylamido)-3-O-benzoyl-4-octadecene-1,3-diol 在 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 12.0h， 以76.2%的产率得到(2S,3R,4E)-[4'-O-(β-D-galactopyranosyl)-β-D-glucopyranosyl]-(1'->1)-2-(hexadecanoylamido)-4-octadecene-1,3-diol
  参考文献：
  名称：

  Efficient Syntheses of a Series of Glycosphingolipids with 1,2‐trans‐Glycosidic Linkages

  摘要：

  A series of glycosphingolipids with 1,2-trans-glycosidic linkages were synthesized in the presence of neighboring group participation using trichloroacetimidates as glycosyl donors and an azido-sphingosine as the glycosyl acceptor. During the preparation of the target compounds, it was found that the alpha-L-arabinopyranosyl unit in target 7e and intermediates 7b - 7d existed in the C-1(4) conformation and that the b-L-fucopyranosyl unit in 10e adopted the C-4(1) conformation.

  DOI：

  10.1080/07328300600859825
• 作为产物：
  描述：

  (2S,3R,4E)-3-O-benzoyl-2-hexadecanamido-4-octadecene-1,3-diol 、 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzoyl-α-D-glucopyranosyl trichloroacetimidate 在 三氟化硼乙醚 作用下， 以40%的产率得到(2S,3R,4E)-[2',3',6'-tri-O-benzoyl-4'-O-(2'',3'',4'',6''-tetra-O-benzoyl-β-D-galactopyranosyl)-β-D-glucopyranosyl]-(1'->1)-2-(hexadecanoylamido)-3-O-benzoyl-4-octadecene-1,3-diol
  参考文献：
  名称：

  Efficient Syntheses of a Series of Glycosphingolipids with 1,2‐trans‐Glycosidic Linkages

  摘要：

  A series of glycosphingolipids with 1,2-trans-glycosidic linkages were synthesized in the presence of neighboring group participation using trichloroacetimidates as glycosyl donors and an azido-sphingosine as the glycosyl acceptor. During the preparation of the target compounds, it was found that the alpha-L-arabinopyranosyl unit in target 7e and intermediates 7b - 7d existed in the C-1(4) conformation and that the b-L-fucopyranosyl unit in 10e adopted the C-4(1) conformation.

  DOI：

  10.1080/07328300600859825