methyl 6-O-(3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-glucofuranos-3-yl)-2,3-O-isopropylidene-5-O-methyl-α-D-mannofuranoside | 196859-71-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6-O-(3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-glucofuranos-3-yl)-2,3-O-isopropylidene-5-O-methyl-α-D-mannofuranoside
• CAS: 196859-71-9
• 化学式: C₂₃H₃₈O₁₁
• 分子量: 490.548
• InChiKey: GIEQPAACKKYBJV-SCXCTZIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.31
• 重原子数：
  34.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  101.53
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  methyl 6-O-(3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-glucofuranos-3-yl)-2,3-O-isopropylidene-5-O-methyl-α-D-mannofuranoside 在 吡啶 、 氯化亚砜 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 18.33h， 生成 methyl 6-O-(3-deoxy-1,2-O-isopropylidene-5,6-O-sulfinyl-α-D-glucofuranos-3-yl)-2,3-O-isopropylidene-5-O-methyl-α-D-mannofuranoside
  参考文献：
  名称：

  Synthesis of Ether Linked Pseudo-OligosaccharidesVia5,6-Cyclic Sulfate Derivatives of Protected Manno and Glucofuranose

  摘要：

  C-6 ring opening of 5,6-cyclic sulfate derivatives of protected manno and glucofuranose with carbohydrate alkoxides gave ether linked pseudo-di or trisaccharides. Use of methyl 2,3-O-isopropylidene-5,6-O-sulfuryl-alpha-D-mannofuranoside 1 led to protected pseudo-disaccharide D-Glcf-(3-->6)-D-Manf-(5-->6)-D-Manf 4 and protected pseudo-trisaccharide D-Manf-(6-->3)-D-Glcf-(6-->3)-D-Glcf 11 derivatives in 66% and 41% overall yields, respectively.

  DOI：

  10.1080/07328309708005739
• 作为产物：
  描述：

  Lithium; (3aR,5S,6S,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-olate 在 硫酸 、 sodium hydride 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 N,N-二甲基甲酰胺 为溶剂， 生成 methyl 6-O-(3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-glucofuranos-3-yl)-2,3-O-isopropylidene-5-O-methyl-α-D-mannofuranoside
  参考文献：
  名称：

  Synthesis of Ether Linked Pseudo-OligosaccharidesVia5,6-Cyclic Sulfate Derivatives of Protected Manno and Glucofuranose

  摘要：

  C-6 ring opening of 5,6-cyclic sulfate derivatives of protected manno and glucofuranose with carbohydrate alkoxides gave ether linked pseudo-di or trisaccharides. Use of methyl 2,3-O-isopropylidene-5,6-O-sulfuryl-alpha-D-mannofuranoside 1 led to protected pseudo-disaccharide D-Glcf-(3-->6)-D-Manf-(5-->6)-D-Manf 4 and protected pseudo-trisaccharide D-Manf-(6-->3)-D-Glcf-(6-->3)-D-Glcf 11 derivatives in 66% and 41% overall yields, respectively.

  DOI：

  10.1080/07328309708005739