1,2-O-Isopropylidene-3-O-(2-naphthylmethyl)-4,5-O-<(1'R)-trans-3'-phenyl-2'-propen-1'-yl>-β-D-fructopyranose | 167482-47-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,2-O-Isopropylidene-3-O-(2-naphthylmethyl)-4,5-O-<(1'R)-trans-3'-phenyl-2'-propen-1'-yl>-β-D-fructopyranose
• 英文别名: 1,2-O-Isopropylidene-3-O-(2-naphthylmethyl)-4,5-O-((1'R)-trans-3'-phenyl-2'-propen-1'-yl)-β-D-fructopyranose；(2'R,3'aR,4S,7'S,7'aR)-2,2-dimethyl-7'-(naphthalen-2-ylmethoxy)-2'-[(E)-2-phenylethenyl]spiro[1,3-dioxolane-4,6'-3a,4,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran]
• CAS: 167482-47-5
• 化学式: C₂₉H₃₀O₆
• 分子量: 474.554
• InChiKey: FVDMOIDHODYNLD-XCQSDDIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  35
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  1,2-O-Isopropylidene-3-O-(2-naphthylmethyl)-4,5-O-<(1'R)-trans-3'-phenyl-2'-propen-1'-yl>-β-D-fructopyranose 在 sodium tetrahydroborate 、 diethylzinc 、 溶剂黄146 作用下， 以 正己烷 、 1,2-二氯乙烷 为溶剂， 反应 25.25h， 生成 (1S,2S)-反式-1-(羟甲基)-2-苯基环丙烷
  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 4-甲基苯磺酸吡啶 、 sodium hydride 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 37.5h， 生成 1,2-O-Isopropylidene-3-O-(2-naphthylmethyl)-4,5-O-<(1'R)-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.