3-O-(diethoxythionophosphoryl)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose | 273386-17-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-O-(diethoxythionophosphoryl)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose
• 英文别名: [(3aR,5R,6S,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl]oxy-diethoxy-sulfidophosphanium
• CAS: 273386-17-7
• 化学式: C₁₆H₂₉O₈PS
• 分子量: 412.441
• InChiKey: JSNDHTXGULHFRN-RKQHYHRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  74.8
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3-O-(diethoxythionophosphoryl)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 在 盐酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 0.5h， 以72%的产率得到3-O-(diethoxythionophosphoryl)-1,2-O-isopropylidene-α-D-glucofuranose
  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：

  O,O-二乙基硫代磷酰氯 、 双丙酮葡萄糖 在 potassium tert-butylate 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以85%的产率得到3-O-(diethoxythionophosphoryl)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose
  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

• Autocleavage of<i>O</i>-Isopropylidene Protected<i>O</i>-Phosphono- and<i>O</i>- Thionophosphono Esters of Sugars
  作者：Denis Postel、Gino Ronco、Pierre Villa

  DOI：10.1080/07328300008544073

  日期：2000.1

  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.