(2R)-2,3-epoxypropyl 2,3-di-O-benzyl-4,6-O-(S)-benzylidene-β-D-galactopyranoside | 1221234-62-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R)-2,3-epoxypropyl 2,3-di-O-benzyl-4,6-O-(S)-benzylidene-β-D-galactopyranoside
• CAS: 1221234-62-3
• 化学式: C₃₀H₃₂O₇
• 分子量: 504.58
• InChiKey: RLDONATUCQMYRT-ISDDDRIGSA-N

反应信息

• 作为产物：
  描述：

  allyl 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)-2,3-epoxypropyl 2,3-di-O-benzyl-4,6-O-(S)-benzylidene-β-D-galactopyranoside 、 (2R)-2,3-epoxypropyl 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