(2S)-3-methyl-2,3-methylidenebutyl 4,6-O-(S)-benzylidene-β-D-galactopyranoside | 1221234-48-5

• 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: (2S)-3-methyl-2,3-methylidenebutyl 4,6-O-(S)-benzylidene-β-D-galactopyranoside
• 英文别名: (2S,4aR,6R,7R,8R,8aR)-6-[[(1S)-2,2-dimethylcyclopropyl]methoxy]-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-7,8-diol
• CAS: 1221234-48-5
• 化学式: C₁₉H₂₆O₆
• 分子量: 350.412
• InChiKey: LPEASMXODKXDLH-RTPSORCZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  二碘甲烷 、 3-methyl-2-butenyl 4,6-O-(S)-benzylidene-β-D-galactopyranoside 在 diethylzinc 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 生成 (2R)-3-methyl-2,3-methylidenebutyl 4,6-O-(S)-benzylidene-β-D-galactopyranoside 、 (2S)-3-methyl-2,3-methylidenebutyl 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

文献信息

• Alkenyl β-d-galactopyranoside derivatives as efficient chiral templates in stereoselective cyclopropanation and epoxidation reactions
  作者：José M. Vega-Pérez、Ignacio Periñán、Carlos Palo-Nieto、Margarita Vega-Holm、Fernando Iglesias-Guerra

  DOI：10.1016/j.tetasy.2009.12.003

  日期：2010.1

  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.