1,2-O-isopropylidene-α-L-allofuranose | 1338054-27-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2-O-isopropylidene-α-L-allofuranose
• 英文别名: (1S)-1-[(3aS,5S,6S,6aS)-6-hydroxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]ethane-1,2-diol
• CAS: 1338054-27-5
• 化学式: C₉H₁₆O₆
• 分子量: 220.222
• InChiKey: BGGCXQKYCBBHAH-WXUMCUSRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  88.4
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,2-O-isopropylidene-α-L-allofuranose 在 sodium tetrahydroborate 、 sodium periodate 作用下， 以 乙醇 、 水 为溶剂， 反应 5.0h， 生成 1,2-O-isopropylidene-α-L-ribofuranose
  参考文献：
  名称：

  Inhibition of Nonmammalian Glycosidases by Azetidine Iminosugars Derived from Stable 3,5-Di-O-triflates of Pentoses

  摘要：

  Efficient ring closure of stable crystalline 3,5-dl-O-triflates of pentofuranosides with amines to form azetidines allowed preliminary evaluation of four-ring iminosugars as glycosidase inhibitors; significant and specific inhibition of nonmammallan alpha-glucosidases Is shown by L-xylo- and L-arabino-iminosugar azetidines.

  DOI：

  10.1021/ol2024482
• 作为产物：
  描述：

  diacetone-D-glucose 在 sodium tetrahydroborate 、 水 、 戴斯-马丁氧化剂 、 溶剂黄146 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 38.25h， 生成 1,2-O-isopropylidene-α-L-allofuranose
  参考文献：
  名称：

  Azetidine Iminosugars from the Cyclization of 3,5-Di-O-triflates of α-Furanosides and of 2,4-Di-O-triflates of β-Pyranosides Derived from Glucose

  摘要：

  Primary amines with either 3,5-di-O-ditriflates of alpha-furanosides or 2,4-di-O-triflates of beta-pyranosides form bicyclic azetidines in high yield.

  DOI：

  10.1021/ol300669v

文献信息

• Inhibition of Nonmammalian Glycosidases by Azetidine Iminosugars Derived from Stable 3,5-Di-<i>O</i>-triflates of Pentoses
  作者：Gabriel M. J. Lenagh-Snow、Noelia Araujo、Sarah F. Jenkinson、Catherine Rutherford、Shinpei Nakagawa、Atsushi Kato、Chu-Yi Yu、Alexander C. Weymouth-Wilson、George W. J. Fleet

  DOI：10.1021/ol2024482

  日期：2011.11.4

  Efficient ring closure of stable crystalline 3,5-dl-O-triflates of pentofuranosides with amines to form azetidines allowed preliminary evaluation of four-ring iminosugars as glycosidase inhibitors; significant and specific inhibition of nonmammallan alpha-glucosidases Is shown by L-xylo- and L-arabino-iminosugar azetidines.
• Azetidine Iminosugars from the Cyclization of 3,5-Di-<i>O</i>-triflates of α-Furanosides and of 2,4-Di-<i>O</i>-triflates of β-Pyranosides Derived from Glucose
  作者：Gabriel M. J. Lenagh-Snow、Noelia Araújo、Sarah F. Jenkinson、R. Fernando Martínez、Yousuke Shimada、Chu-Yi Yu、Atsushi Kato、George W. J. Fleet

  DOI：10.1021/ol300669v

  日期：2012.4.20

  Primary amines with either 3,5-di-O-ditriflates of alpha-furanosides or 2,4-di-O-triflates of beta-pyranosides form bicyclic azetidines in high yield.