9-decenyl 2,3,5,6-tetra-O-benzoyl-α-D-galactofuranoside | 1438222-86-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 9-decenyl 2,3,5,6-tetra-O-benzoyl-α-D-galactofuranoside
• CAS: 1438222-86-6
• 化学式: C₄₄H₄₆O₁₀
• 分子量: 734.843
• InChiKey: GXBBGKUCARCJOP-FGUWLDAFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.18
• 重原子数：
  54.0
• 可旋转键数：
  20.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  123.66
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为产物：
  描述：

  1,2,3,5,6-penta-O-benzoyl-D-galactofuranose 在 碘代三甲硅烷 、 四氯化锡 、 zinc(II) iodide 作用下， 以 二氯甲烷 为溶剂， 反应 0.42h， 生成 9-decenyl 2,3,5,6-tetra-O-benzoyl-β-D-galactofuranoside 、 9-decenyl 2,3,5,6-tetra-O-benzoyl-α-D-galactofuranoside
  参考文献：
  名称：

  Synthetic tools for the characterization of galactofuranosyl transferases: glycosylations via acylated glycosyl iodides

  摘要：

  With the aim of developing synthetic tools for the characterization of galactofuranosyltransferases, the synthesis of 9-decenyl glycosides of D-Manp, D-Galf, and beta-D-Galf-(1 -> 3)-D-Manp was targeted. The interest in the alkenyl aglycone arises via potential conjugation reactions, once the terminal double bond has been conveniently functionalized. The glycosylation of beta-D-Galf-(1 -> 3)-D-Manp was attempted by two different approaches: the trichloroacetimidate method and the glycosylation via the glycosyl iodide. The conditions for the latter were established on the basis of glycosylation assays of per-O-acetylmannose. On the other hand, the study of glycosylation reactions via per-O-benzoylated galactofuranosyl iodide confirms the versatility of glycosyl iodides as donors. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.03.032