3-O-Benzyl-1,2-O-isopropylidene-4,5-O-<(1'S)-trans-3'-phenyl-2'-propen-1'-yl>-β-D-fructopyranose | 167612-51-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: 3-O-Benzyl-1,2-O-isopropylidene-4,5-O-<(1'S)-trans-3'-phenyl-2'-propen-1'-yl>-β-D-fructopyranose
• 英文别名: (2'S,3'aR,4S,7'S,7'aR)-2,2-dimethyl-2'-[(E)-2-phenylethenyl]-7'-phenylmethoxyspiro[1,3-dioxolane-4,6'-3a,4,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran]
• CAS: 167612-51-3
• 化学式: C₂₅H₂₈O₆
• 分子量: 424.494
• InChiKey: LYHGZAOFDNKFLA-WHPFVURBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  二碘甲烷 、 3-O-Benzyl-1,2-O-isopropylidene-4,5-O-<(1'S)-trans-3'-phenyl-2'-propen-1'-yl>-β-D-fructopyranose 在 diethylzinc 作用下， 以 正己烷 、 1,2-二氯乙烷 为溶剂， 反应 24.0h， 以82%的产率得到(2'S,3'aR,4S,7'S,7'aR)-2,2-dimethyl-2'-[(1S,2S)-2-phenylcyclopropyl]-7'-phenylmethoxyspiro[1,3-dioxolane-4,6'-3a,4,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran]
  参考文献：
  名称：

  Asymmetric Cyclopropanation Using New Chiral Auxiliaries Derived from D-Fructose

  摘要：

  Acetals of alpha,beta-unsaturated aldehydes with 3-O-alkylated derivatives of 1,2-O-isopropylidene-beta-D-fructopyranose and 1,2-O-isopropylidene-beta-D-psicopyranose, which are readily available from D-fructose, were cyclopropanated with Et(2)Zn and CH2I2 with good diastereoselectivity. The effects of structure of the acetals on enantioselectivity were examined.

  DOI：

  10.1021/jo00108a018
• 作为产物：
  描述：

  3-O-benzyl-1,2:4,5-di-O-isopropylidene-β-D-fructopyranose 在 4-甲基苯磺酸吡啶 、 溶剂黄146 作用下， 以 苯 为溶剂， 反应 36.0h， 生成 3-O-Benzyl-1,2-O-isopropylidene-4,5-O-<(1'S)-trans-3'-phenyl-2'-propen-1'-yl>-β-D-fructopyranose
  参考文献：
  名称：

  Asymmetric Cyclopropanation Using New Chiral Auxiliaries Derived from D-Fructose

  摘要：

  Acetals of alpha,beta-unsaturated aldehydes with 3-O-alkylated derivatives of 1,2-O-isopropylidene-beta-D-fructopyranose and 1,2-O-isopropylidene-beta-D-psicopyranose, which are readily available from D-fructose, were cyclopropanated with Et(2)Zn and CH2I2 with good diastereoselectivity. The effects of structure of the acetals on enantioselectivity were examined.

  DOI：

  10.1021/jo00108a018

文献信息

• Asymmetric Cyclopropanation Using New Chiral Auxiliaries Derived from D-Fructose
  作者：Jahyo Kang、Geun Jho Lim、Suk Kyoon Yoon、Moohi Yoo Kim

  DOI：10.1021/jo00108a018

  日期：1995.2

  Acetals of alpha,beta-unsaturated aldehydes with 3-O-alkylated derivatives of 1,2-O-isopropylidene-beta-D-fructopyranose and 1,2-O-isopropylidene-beta-D-psicopyranose, which are readily available from D-fructose, were cyclopropanated with Et(2)Zn and CH2I2 with good diastereoselectivity. The effects of structure of the acetals on enantioselectivity were examined.