3-O-(2'-methyl-2'-propenyl)-1,2-O-isopropylidene-α-D-arabinopentodialdo-1,4-furanose oxime | 499139-12-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-O-(2'-methyl-2'-propenyl)-1,2-O-isopropylidene-α-D-arabinopentodialdo-1,4-furanose oxime
• CAS: 499139-12-7
• 化学式: C₁₂H₁₉NO₅
• 分子量: 257.287
• InChiKey: QTXMENMCHZHAMU-LMLFDSFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.28
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  69.51
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3-O-(2'-methyl-2'-propenyl)-1,2-O-isopropylidene-α-D-arabinopentodialdo-1,4-furanose oxime 在 镍 sodium hypochlorite 、 氢气 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 (3aR,3bR,6S,7aS,8aR)-6-Hydroxymethyl-2,2,6-trimethyl-hexahydro-[1,3]dioxolo[4,5]furo[3,2-b]pyran-7-one
  参考文献：
  名称：

  Asymmetric epoxidation catalyzed by d-glucose-derived uloses

  摘要：

  Three ulose catalysts (1-3) were prepared from D-glucose via an intramolecular nitrile oxide cycloaddition (INOC) as the key step. The enantioselectivity of ulose 2 and 3 in asymmetric epoxidation was poor (up to 26% ee). Ulose 1 afforded good chemical yields (up to 83% yield) and the enantiomeric excess is up to 71% for the formation of (-)-trans-stilbene oxide. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00577-x
• 作为产物：
  描述：

  2,2-dimethyl-6-(2-methylallyloxy)-(3aR,5S,6R,6aR)-perhydrofuro[2,3-d][1,3]dioxole-5-carbaldehyde 在 盐酸羟胺 、 碳酸氢钠 作用下， 以 乙醇 为溶剂， 以1.25 g的产率得到3-O-(2'-methyl-2'-propenyl)-1,2-O-isopropylidene-α-D-arabinopentodialdo-1,4-furanose oxime
  参考文献：
  名称：

  Asymmetric epoxidation catalyzed by d-glucose-derived uloses

  摘要：

  Three ulose catalysts (1-3) were prepared from D-glucose via an intramolecular nitrile oxide cycloaddition (INOC) as the key step. The enantioselectivity of ulose 2 and 3 in asymmetric epoxidation was poor (up to 26% ee). Ulose 1 afforded good chemical yields (up to 83% yield) and the enantiomeric excess is up to 71% for the formation of (-)-trans-stilbene oxide. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00577-x