(E)-2-methyl-3-phenyl-2-propenyl 3-O-benzyl-4,6-O-(S)-benzylidene-β-D-galactopyranoside | 1221234-46-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: (E)-2-methyl-3-phenyl-2-propenyl 3-O-benzyl-4,6-O-(S)-benzylidene-β-D-galactopyranoside
• CAS: 1221234-46-3
• 化学式: C₃₀H₃₂O₆
• 分子量: 488.58
• InChiKey: GXSHZBRQKOQILH-FTODKGATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.89
• 重原子数：
  36.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  66.38
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (E)-2-methyl-3-phenyl-2-propenyl 3-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-2-methyl-3-phenylpropyl 3-O-benzyl-4,6-O-(S)-benzylidene-β-D-galactopyranoside 、 (2R,3R)-2,3-epoxy-2-methyl-3-phenylpropyl 3-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)-2-methyl-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， 反应 0.33h， 以60%的产率得到(E)-2-methyl-3-phenyl-2-propenyl 3-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