benzyl 6-O-(3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-glucofuranos-3-yl)-2,3-O-isopropylidene-α-D-mannofuranoside | 196859-69-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 6-O-(3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-glucofuranos-3-yl)-2,3-O-isopropylidene-α-D-mannofuranoside
• CAS: 196859-69-5
• 化学式: C₂₈H₄₀O₁₁
• 分子量: 552.619
• InChiKey: XMJQKOTWJGDKNA-GBIOGVGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.22
• 重原子数：
  39.0
• 可旋转键数：
  8.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  112.53
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  benzyl 6-O-(3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-glucofuranos-3-yl)-2,3-O-isopropylidene-α-D-mannofuranoside 在 palladium on activated charcoal 甲酸铵 作用下， 以 甲醇 为溶剂， 反应 1.58h， 以100%的产率得到6-O-(3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-glucofuranos-3-yl)-2,3-O-isopropylidene-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：

  benzyl 2,3-O-isopropylidene-5,6-O-sulfinyl-α-D-mannofuranoside 在 ruthenium trichloride 、 sodium periodate 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 3.83h， 生成 benzyl 6-O-(3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-glucofuranos-3-yl)-2,3-O-isopropylidene-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