benzyl 2,4,6-tri-O-benzoyl-3-O-chloroacetyl-β-D-glucopyranoside | 195063-72-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: benzyl 2,4,6-tri-O-benzoyl-3-O-chloroacetyl-β-D-glucopyranoside
• CAS: 195063-72-0
• 化学式: C₃₆H₃₁ClO₁₀
• 分子量: 659.089
• InChiKey: OFSYGRULIWJSRQ-LZLCOJQVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.39
• 重原子数：
  47.0
• 可旋转键数：
  12.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  123.66
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  benzyl 2,4,6-tri-O-benzoyl-3-O-chloroacetyl-β-D-glucopyranoside 在 2,4,6-三甲基吡啶 、 3 A molecular sieve 、 silver trifluoromethanesulfonate 、 硫脲 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 20.5h， 生成
  参考文献：
  名称：

  Rhizobial saccharides. Part. 4. Unusual Reactivity of Pyruvated Glycosyl Donors during construction of rhizobial exopolysaccharide fragments

  摘要：

  Two pyruvated galactosyl donors, 2,3-di-O-benzoyl-4,6-0-[1-(R)-methoxycarbonyl(ethylidene)]-alpha-D-galactopyranosyl chloride (6) and trichloroacetimidate 13, were coupled to position 3 of suitably protected mono and disaccharide benzyl glucoside accepters. For both donors, an unusual high content of the alpha-(1-->3)-linked products was obtained. The corresponding beta-(1-->3)-linked di- and trisaccharides are related to exopolysaccharides of Rhizobium leguminosarum.

  DOI：

  10.1002/prac.19973390196
• 作为产物：
  描述：

  1,2,4,6-tetra-O-benzoyl-3-O-chloroacetyl-β-D-glucopyranoside 在 2,4,6-三甲基吡啶 、 3 A molecular sieve 、 氢溴酸 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 1.67h， 生成 benzyl 2,4,6-tri-O-benzoyl-3-O-chloroacetyl-β-D-glucopyranoside
  参考文献：
  名称：

  Rhizobial saccharides. Part. 4. Unusual Reactivity of Pyruvated Glycosyl Donors during construction of rhizobial exopolysaccharide fragments

  摘要：

  Two pyruvated galactosyl donors, 2,3-di-O-benzoyl-4,6-0-[1-(R)-methoxycarbonyl(ethylidene)]-alpha-D-galactopyranosyl chloride (6) and trichloroacetimidate 13, were coupled to position 3 of suitably protected mono and disaccharide benzyl glucoside accepters. For both donors, an unusual high content of the alpha-(1-->3)-linked products was obtained. The corresponding beta-(1-->3)-linked di- and trisaccharides are related to exopolysaccharides of Rhizobium leguminosarum.

  DOI：

  10.1002/prac.19973390196