O-{2,3-di-O-benzoyl-4,6-O-[(R)-1-methoxycarbonyl(ethylidene)]-α-D-galactopyranosyl}-(1->3)-2,4,6-tri-O-benzoyl-β-D-glucopyranosyl-(1->3)-2-O-benzoyl-4,6-O-[(S)-1-methoxycarbonyl(ethylidene)]-α-D-glucopyranose | 195063-79-7

• 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: O-{2,3-di-O-benzoyl-4,6-O-[(R)-1-methoxycarbonyl(ethylidene)]-α-D-galactopyranosyl}-(1->3)-2,4,6-tri-O-benzoyl-β-D-glucopyranosyl-(1->3)-2-O-benzoyl-4,6-O-[(S)-1-methoxycarbonyl(ethylidene)]-α-D-glucopyranose
• CAS: 195063-79-7
• 化学式: C₆₈H₆₄O₂₆
• 分子量: 1297.24
• InChiKey: LABDFBXIKGIVOW-YRMWKZKQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.52
• 重原子数：
  94.0
• 可旋转键数：
  19.0
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  313.7
• 氢给体数：
  1.0
• 氢受体数：
  26.0

反应信息

• 作为反应物：
  描述：

  三氯乙腈 、 O-{2,3-di-O-benzoyl-4,6-O-[(R)-1-methoxycarbonyl(ethylidene)]-α-D-galactopyranosyl}-(1->3)-2,4,6-tri-O-benzoyl-β-D-glucopyranosyl-(1->3)-2-O-benzoyl-4,6-O-[(S)-1-methoxycarbonyl(ethylidene)]-α-D-glucopyranose 在 potassium carbonate 作用下， 反应 10.0h， 生成 O-{2,3-di-O-benzoyl-4,6-O-[(R)-1-methoxycarbonyl(ethylidene)]-α-D-galactopyranosyl}-(1->3)-2,4,6-tri-O-benzoyl-β-D-glucopyranosyl-(1->3)-2-O-benzoyl-4,6-O-[(S)-1-methoxycarbonyl(ethylidene)]-β-D-glucopyranosyl trichloroacetimidate 、 O-{2,3-di-O-benzoyl-4,6-O-[(R)-1-methoxycarbonyl(ethylidene)]-α-D-galactopyranosyl}-(1->3)-2,4,6-tri-O-benzoyl-β-D-glucopyranosyl-(1->3)-2-O-benzoyl-4,6-O-[(S)-1-methoxycarbonyl(ethylidene)]-α-D-glucopyranosyl trichloroacetimidate
  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：

  2,4,6-tri-O-benzoyl-3-O-chloroacetyl-α-D-glucopyranosyl bromide 在 palladium on activated charcoal 2,4,6-三甲基吡啶 、 三氟甲磺酸三甲基硅酯 、 3 A molecular sieve 、 氢气 、 silver trifluoromethanesulfonate 、 硫脲 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 68.08h， 生成 O-{2,3-di-O-benzoyl-4,6-O-[(R)-1-methoxycarbonyl(ethylidene)]-α-D-galactopyranosyl}-(1->3)-2,4,6-tri-O-benzoyl-β-D-glucopyranosyl-(1->3)-2-O-benzoyl-4,6-O-[(S)-1-methoxycarbonyl(ethylidene)]-α-D-glucopyranose
  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