1,3-di-O-benzyl-2-O-(6-O-octanoyl-β-D-glucopyranosyl)-sn-glycerol | 250608-21-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: 1,3-di-O-benzyl-2-O-(6-O-octanoyl-β-D-glucopyranosyl)-sn-glycerol
• CAS: 250608-21-0
• 化学式: C₃₁H₄₄O₉
• 分子量: 560.685
• InChiKey: OQFOSGZOEJZXTN-OVFXHNNVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.52
• 重原子数：
  40.0
• 可旋转键数：
  18.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  123.91
• 氢给体数：
  3.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  1,3-di-O-benzyl-2-O-(6-O-octanoyl-β-D-glucopyranosyl)-sn-glycerol 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以98%的产率得到2-O-(6-O-octanoyl-β-D-glucopyranosyl)-sn-glycerol
  参考文献：
  名称：

  Chemoenzymatic synthesis and antitumor promoting activity of 6′- and 3-esters of 2- O -β- d -glucosylglycerol

  摘要：

  Through a simple chemoenzymatic approach 6'- and 3-esters of 2-O-beta-D-glucosylglycerol 1, with short-medium length fatty acid acyl chains, were prepared. The study of their in vitro antitumor promoting effect on Epstein-Barr virus early antigen (EBV-EA) activation, in comparison with that of the 1-esters previously described, confirms the significant activity of such monoacylated glycoglycerolipid analogues and establishes for the glucose series that the 1-substitution and the hexanoyl chain are the proper structural features for the maximum activity.

  DOI：

  10.1016/s0968-0896(99)00137-6
• 作为产物：
  描述：

  1,3-di-O-benzyl-2-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-sn-glycerol 在 Pseudomonas cepacia lipase 、 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 26.0h， 生成 1,3-di-O-benzyl-2-O-(6-O-octanoyl-β-D-glucopyranosyl)-sn-glycerol
  参考文献：
  名称：

  Chemoenzymatic synthesis and antitumor promoting activity of 6′- and 3-esters of 2- O -β- d -glucosylglycerol

  摘要：

  Through a simple chemoenzymatic approach 6'- and 3-esters of 2-O-beta-D-glucosylglycerol 1, with short-medium length fatty acid acyl chains, were prepared. The study of their in vitro antitumor promoting effect on Epstein-Barr virus early antigen (EBV-EA) activation, in comparison with that of the 1-esters previously described, confirms the significant activity of such monoacylated glycoglycerolipid analogues and establishes for the glucose series that the 1-substitution and the hexanoyl chain are the proper structural features for the maximum activity.

  DOI：

  10.1016/s0968-0896(99)00137-6