1-O-(diethoxyphosphoryl)-2,3:4,5-di-O-isopropylidene-α-D-fructopyranose | 273386-30-4

• 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: 1-O-(diethoxyphosphoryl)-2,3:4,5-di-O-isopropylidene-α-D-fructopyranose
• CAS: 273386-30-4
• 化学式: C₁₆H₂₉O₉P
• 分子量: 396.375
• InChiKey: TXCIMIOAKREBHV-FOCJUVANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.58
• 重原子数：
  26.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  90.91
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  1-O-(diethoxyphosphoryl)-2,3:4,5-di-O-isopropylidene-α-D-fructopyranose 以 水 为溶剂， 反应 1.2h， 以61%的产率得到1-O-(diethoxyphosphoryl)-2,3-isopropylidene-α-D-fructopyranose
  参考文献：
  名称：

  Autocleavage ofO-Isopropylidene ProtectedO-Phosphono- andO- Thionophosphono Esters of Sugars

  摘要：

  Phosphorylation of D-glucose, D-galactose, D-fructose, glycerol and xylitol acetals with diethoxy- or diphenoxy(thiono)phosphoryl chloride gave the corresponding esters. A novel method of partially and fully deprotecting these compounds, which we have called "autocatalytic cleavage", was effected by simply refluxing in water. Antifungal and insecticidal properties of these compounds are presented.

  DOI：

  10.1080/07328300008544073
• 作为产物：
  描述：

  果糖二丙酮 、 氯磷酸二乙酯 在 potassium tert-butylate 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以68%的产率得到1-O-(diethoxyphosphoryl)-2,3:4,5-di-O-isopropylidene-α-D-fructopyranose
  参考文献：
  名称：

  Autocleavage ofO-Isopropylidene ProtectedO-Phosphono- andO- Thionophosphono Esters of Sugars

  摘要：

  Phosphorylation of D-glucose, D-galactose, D-fructose, glycerol and xylitol acetals with diethoxy- or diphenoxy(thiono)phosphoryl chloride gave the corresponding esters. A novel method of partially and fully deprotecting these compounds, which we have called "autocatalytic cleavage", was effected by simply refluxing in water. Antifungal and insecticidal properties of these compounds are presented.

  DOI：

  10.1080/07328300008544073

文献信息

• Site‐Selective Direct Intermolecular C(<i>sp</i>³)−H Alkylation of Saccharides and Switching of Reaction Sites by Changing Photocatalysts
  作者：Yanru Li、Yoichiro Kuninobu

  DOI：10.1002/adsc.202300329

  日期：2023.8.10

  compatible with several electron-deficient alkenes and saccharides, and provides C-saccharides in good yields. Furthermore, the monoalkylated product was obtained in excellent yield, even on the gram scale, under TBADT photocatalysis. Applicability was demonstrated by site-selective C(sp3)−H alkylation of glycosyl derivatives. The reactions proceed via a site-selective hydrogen atom transfer between the photocatalyst

  我们利用蒽醌和十钨酸四丁基铵 (TBADT) 的光催化作用，开发了糖与缺电子烯烃的位点选择性分子间 C( sp 3 )−H 烷基化。蒽醌催化的C( sp 3 )−H烷基化的主要反应位点由CH键的弱度决定。通过将光催化剂改为TBADT可以切换反应位点，并且位点选择性由体积较大的TBADT光催化剂和糖类取代基之间的空间位阻控制。该反应与多种缺电子烯烃和糖类相容，并提供C-糖类收率良好。此外，在 TBADT 光催化下，单烷基化产物的产率很高，甚至是克级的。通过糖基衍生物的位点选择性 C( sp 3 )−H 烷基化证明了适用性。该反应通过光催化剂和糖之间的位点选择性氢原子转移进行，产生的碳自由基与缺电子烯烃反应生成烷基化产物。