1-O-acetyl-2,3,4-tri-O-benzyl-6,7-dideoxy-D-galacto-hept-6-enopyranose | 139285-92-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-O-acetyl-2,3,4-tri-O-benzyl-6,7-dideoxy-D-galacto-hept-6-enopyranose
• 英文别名: [(3R,4S,5S,6R)-6-ethenyl-3,4,5-tris(phenylmethoxy)oxan-2-yl] acetate
• CAS: 139285-92-0
• 化学式: C₃₀H₃₂O₆
• 分子量: 488.58
• InChiKey: UERMETKVYXUUIS-LSZMOXLZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  36
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-O-acetyl-2,3,4-tri-O-benzyl-6,7-dideoxy-D-galacto-hept-6-enopyranose 在 四(三苯基膦)钯 、 diethylzinc 、 zinc(II) chloride 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 24.0h， 生成 (1S,2S,3S,4S,5R)-2,3,4-tri-O=benzyl-5-ethenylcyclopentanetetraol 、 (1R,2S,3S,4S,5R)-tri-O-benzyl-5-ethenylcyclopentanetetraol 、 (1S,2S,3S,4S,5S)-2,3,4-tri-O=benzyl-5-ethenylcyclopentanetetraol
  参考文献：
  名称：

  Direct carbohydrate to carbocycle conversions via intramolecular allylation with Et2Zn/Pd(0)

  摘要：

  Treatment of 5-vinylpyranosides with Et2Zn and catalytic Pd(0), in the presence of ZnCl2, results in the formation of 5-membered carbocyclic products. This carbohydrate ring-contraction features an intramolecular allylation of a ring-opened carbohydrate aldehyde by an in situ-generated nucleophilic allylzinc species. The stereoselectivity about vinyl and free hydroxyl groups at the newly created stereogenic centers varies from low to moderate while both its extent and sense are found to depend on particular structural features (e.g. the configuration of the starting carbohydrate). (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00825-1