benzyl O-(2,4,6-tri-O-benzoyl-β-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4,6-O-<(S)-1-methoxycarbonyl(ethylidene)>-α-D-glucopyranoside | 195063-76-4

• 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 O-(2,4,6-tri-O-benzoyl-β-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4,6-O-<(S)-1-methoxycarbonyl(ethylidene)>-α-D-glucopyranoside
• CAS: 195063-76-4
• 化学式: C₅₁H₄₈O₁₇
• 分子量: 932.932
• InChiKey: WMPQNYALYUOHOW-DGCDOZSNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.24
• 重原子数：
  68.0
• 可旋转键数：
  15.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  207.11
• 氢给体数：
  1.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  benzyl O-(2,4,6-tri-O-benzoyl-β-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4,6-O-<(S)-1-methoxycarbonyl(ethylidene)>-α-D-glucopyranoside 在 palladium on activated charcoal 三氟甲磺酸三甲基硅酯 、 氢气 、 potassium carbonate 作用下， 反应 58.5h， 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-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 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 19.58h， 生成 benzyl O-(2,4,6-tri-O-benzoyl-β-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4,6-O-<(S)-1-methoxycarbonyl(ethylidene)>-α-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
• 作为试剂：
  描述：

  2,3-di-O-benzoyl-4,6-O-<1-(R)-methoxycarbonyl(ethylidene)>-α-D-galactopyranosyl trichloroacetimidate 在 palladium on activated charcoal 三氟甲磺酸三甲基硅酯 、 氢气 、 benzyl O-(2,4,6-tri-O-benzoyl-β-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4,6-O-<(S)-1-methoxycarbonyl(ethylidene)>-α-D-glucopyranoside 作用下， 生成 (2R,4aR,6S,7R,8S,8aS)-7,8-Bis-benzoyloxy-6-(2,2-dichloro-acetoxy)-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxine-2-carboxylic acid methyl ester 、 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