3-deoxy-1,2:5,6-di-O-isopropylidene-(3S)-3,3-C-[(S)-(formyl)ethylene]-α-D-ribo-hexofuranose | 214400-81-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-deoxy-1,2:5,6-di-O-isopropylidene-(3S)-3,3-C-[(S)-(formyl)ethylene]-α-D-ribo-hexofuranose
• CAS: 214400-81-4
• 化学式: C₁₅H₂₂O₆
• 分子量: 298.336
• InChiKey: NYIISWKNAIPUSS-FWGJMNDOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.22
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  63.22
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3-deoxy-1,2:5,6-di-O-isopropylidene-(3S)-3,3-C-[(S)-(formyl)ethylene]-α-D-ribo-hexofuranose 在 palladium on activated charcoal 氢气 、 碳酸氢钠 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以65%的产率得到[(3aR,5S,6R,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2,6-trimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-acetaldehyde
  参考文献：
  名称：

  Synthesis and Application of 3,3-Spirocyclopropane Derivatives Obtained from 1,2:5,6-Di-O-Isopropylidene-α-D-Glucofuranose

  摘要：

  3,3-Spirocyclopropane derivatives (5 and 7) were prepared by three different methods of cyclopropanation starting from 1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose (2). Subsequent radical induced cyclopropane ring opening reaction stereospecifically provided the 3-C-allyl derivative (9). However, activation of the cyclopropyl ring through the aldehyde (10) followed by hydrogenation gave a quaternary chiral derivative (11) which was elaborated to the versatile intermediate (1) by using Bamford-Stevens reaction.

  DOI：

  10.1080/07328309808001887
• 作为产物：
  描述：

  ethyl 2-((3aR,5S,6aR)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyldihydrofuro[2,3-d][1,3]dioxol-6(5H)-ylidene)acetate 在 sodium hydride 、 二异丁基氢化铝 作用下， 以 二甲基亚砜 、 甲苯 为溶剂， 反应 3.0h， 生成 3-deoxy-1,2:5,6-di-O-isopropylidene-(3S)-3,3-C-[(S)-(formyl)ethylene]-α-D-ribo-hexofuranose
  参考文献：
  名称：

  Synthesis and Application of 3,3-Spirocyclopropane Derivatives Obtained from 1,2:5,6-Di-O-Isopropylidene-α-D-Glucofuranose

  摘要：

  3,3-Spirocyclopropane derivatives (5 and 7) were prepared by three different methods of cyclopropanation starting from 1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose (2). Subsequent radical induced cyclopropane ring opening reaction stereospecifically provided the 3-C-allyl derivative (9). However, activation of the cyclopropyl ring through the aldehyde (10) followed by hydrogenation gave a quaternary chiral derivative (11) which was elaborated to the versatile intermediate (1) by using Bamford-Stevens reaction.

  DOI：

  10.1080/07328309808001887