(E)-3-phenyl-2-propenyl 2,3-di-O-benzyl-4,6-O-(S)-benzylidene-β-D-galactopyranoside | 1221234-34-9

• 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: (E)-3-phenyl-2-propenyl 2,3-di-O-benzyl-4,6-O-(S)-benzylidene-β-D-galactopyranoside
• CAS: 1221234-34-9
• 化学式: C₃₆H₃₆O₆
• 分子量: 564.678
• InChiKey: YUEVMMFEWLDZBE-VRBNLOELSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.73
• 重原子数：
  42.0
• 可旋转键数：
  11.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  55.38
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (E)-3-phenyl-2-propenyl 2,3-di-O-benzyl-4,6-O-(S)-benzylidene-β-D-galactopyranoside 在 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 反应 168.0h， 生成 (2S,3S)-2,3-epoxy-3-phenylpropyl 2,3-di-O-benzyl-4,6-O-(S)-benzylidene-β-D-galactopyranoside 、 (2R,3R)-2,3-epoxy-3-phenylpropyl 2,3-di-O-benzyl-4,6-O-(S)-benzylidene-β-D-galactopyranoside
  参考文献：
  名称：

  Alkenyl β-d-galactopyranoside derivatives as efficient chiral templates in stereoselective cyclopropanation and epoxidation reactions

  摘要：

  The synthesis of a wide range of alkenyl 4,6-O-(S)-benzylidene-beta-D-galactopyranosides is described. The cyclopropanation and epoxidation reactions of these compounds were developed. Cyclopropanation reactions took place with high stereoselectivity giving diastereomeric excesses of up to 100%. As a part Of Our aim in studying hydroxyl-directed reactions, their epoxidation with m-CPBA was carried out High diastereomeric excesses (80-100%) were obtained when the hydroxyl group at C-2 of the auxiliary was unprotected The beta-D-galactopyranoside moiety constitutes as an interesting auxiliary, due to its efficient chirality transfer capability as well as providing a way to obtain a variety of glycolipid derivatives (c) 2009 Elsevier Ltd All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.12.003
• 作为产物：
  描述：

  (E)-3-phenyl-2-propenyl 4,6-O-(S)-benzylidene-β-D-galactopyranoside 、 溴甲苯 在 18-冠醚-6 、 potassium hydroxide 作用下， 以 四氢呋喃 为溶剂， 以77%的产率得到(E)-3-phenyl-2-propenyl 2,3-di-O-benzyl-4,6-O-(S)-benzylidene-β-D-galactopyranoside
  参考文献：
  名称：

  Alkenyl β-d-galactopyranoside derivatives as efficient chiral templates in stereoselective cyclopropanation and epoxidation reactions

  摘要：

  The synthesis of a wide range of alkenyl 4,6-O-(S)-benzylidene-beta-D-galactopyranosides is described. The cyclopropanation and epoxidation reactions of these compounds were developed. Cyclopropanation reactions took place with high stereoselectivity giving diastereomeric excesses of up to 100%. As a part Of Our aim in studying hydroxyl-directed reactions, their epoxidation with m-CPBA was carried out High diastereomeric excesses (80-100%) were obtained when the hydroxyl group at C-2 of the auxiliary was unprotected The beta-D-galactopyranoside moiety constitutes as an interesting auxiliary, due to its efficient chirality transfer capability as well as providing a way to obtain a variety of glycolipid derivatives (c) 2009 Elsevier Ltd All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.12.003