1,2-O-Isopropylidene-3-O-(p-phenylbenzyl)-β-D-fructopyranose | 167482-35-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,2-O-Isopropylidene-3-O-(p-phenylbenzyl)-β-D-fructopyranose
• 英文别名: (5S,6S,7R,8R)-2,2-dimethyl-6-[(4-phenylphenyl)methoxy]-1,3,10-trioxaspiro[4.5]decane-7,8-diol
• CAS: 167482-35-1
• 化学式: C₂₂H₂₆O₆
• 分子量: 386.445
• InChiKey: PSNXCBZCCQRZAX-JBPLPALLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,2-O-Isopropylidene-3-O-(p-phenylbenzyl)-β-D-fructopyranose 在 Lindlar catalyst 氢气 、 4-甲基苯磺酸吡啶 作用下， 以 甲醇 、 苯 为溶剂， 反应 8.0h， 生成 1,2-O-Isopropylidene-3-O-(p-phenylbenzyl)-4,5-O-<(1'R)-cis-6'-phenyl-2'-hexen-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
• 作为产物：
  描述：

  1,2;4,5-di-O-isopropylidene-β-D-(-)-fructopyranose 在 sodium hydride 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 13.5h， 生成 1,2-O-Isopropylidene-3-O-(p-phenylbenzyl)-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.