(2S,3R,4E)-2',3',4',6'-tetra-O-benzoyl-β-D-glucopyranosyl-(1'->1)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol | 914803-29-5

• 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',4',6'-tetra-O-benzoyl-β-D-glucopyranosyl-(1'->1)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol
• CAS: 914803-29-5
• 化学式: C₅₉H₆₅N₃O₁₂
• 分子量: 1008.18
• InChiKey: RCVYJALVGJLFRY-TZFYFNNDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.42
• 重原子数：
  74.0
• 可旋转键数：
  29.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  198.72
• 氢给体数：
  0.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  (2S,3R,4E)-2',3',4',6'-tetra-O-benzoyl-β-D-glucopyranosyl-(1'->1)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol 在 sodium methylate 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 22.0h， 生成 glucosylceramide
  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)-2-azido-3-benzoyloxy-4-octadecen-1-ol 、 2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl trichloroacetimidate 在 4 A molecular sieve 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以95%的产率得到(2S,3R,4E)-2',3',4',6'-tetra-O-benzoyl-β-D-glucopyranosyl-(1'->1)-2-azido-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