phenyl O-<2,3-di-O-benzoyl-4,6-O-<(R)-1-(methoxycarbonyl)ethylidene>-β-D-galactopyranosyl>-(1->4)-2,3,6-tri-O-benzoyl-1-thio-β-D-glucopyranoside | 169962-10-1

• 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: phenyl O-<2,3-di-O-benzoyl-4,6-O-<(R)-1-(methoxycarbonyl)ethylidene>-β-D-galactopyranosyl>-(1->4)-2,3,6-tri-O-benzoyl-1-thio-β-D-glucopyranoside
• 英文别名: methyl (2R,4aR,6S,7R,8S,8aS)-7,8-dibenzoyloxy-6-[(2R,3R,4S,5R,6S)-4,5-dibenzoyloxy-2-(benzoyloxymethyl)-6-phenylsulfanyloxan-3-yl]oxy-2-methyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-2-carboxylate
• CAS: 169962-10-1
• 化学式: C₅₇H₅₀O₁₇S
• 分子量: 1039.08
• InChiKey: UKKRHZBCWNLQMG-DTBNBNTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.9
• 重原子数：
  75
• 可旋转键数：
  22
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  229
• 氢给体数：
  0
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  phenyl O-<2,3-di-O-benzoyl-4,6-O-<(R)-1-(methoxycarbonyl)ethylidene>-β-D-galactopyranosyl>-(1->4)-2,3,6-tri-O-benzoyl-1-thio-β-D-glucopyranoside 在 三氟化硼乙醚 、 水 、 溴 、 potassium carbonate 作用下， 以 四氯化碳 、 二氯甲烷 为溶剂， 反应 25.08h， 生成 5-<(benzyloxycarbonyl)amino>pentyl O-<2,3-di-O-benzoyl-4,6-O-<(R)-1-methoxycarbonyl(ethylidene)>-β-D-galactopyranosyl>-(1->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranoside
  参考文献：
  名称：

  Efficient blockwise synthesis of pyruvated di- and trisaccharide fragments related to Klebsiella K26 capsular polysaccharides

  摘要：

  Pyruvated di- and trisaccharide fragments representing the immunodominant side chains of Klebsiella K26 capsular polysaccharides are prepared. Phenyl 4',6'-O-benzylidene-1-thio-beta-D-lactoside (1) is converted in 4 steps into the corresponding pyruvated 1-thio-lactoside (2) and transformed into the imidate (4). Coupling of the latter with Z-protected 5-aminopentanol gives the pyruvated disaccharide fragment (6) upon deblocking. Similarly, imidate (4) is coupled to allyl 2,3-di-O-benzoyl-3-O-(1-fluoro-1,1,3,3-tetraisopropyl-1,3-disiloxane-3-yl)-alpha-D-glucopyranoside (8) to give the corresponding trisaccharide fragment upon deblocking.

  DOI：

  10.1002/prac.19963380148
• 作为产物：
  描述：

  丙酮酸甲酯 、 phenyl 2,3,6-tri-O-benzoyl-4-O-(2,3-di-O-benzoyl-β-D-galactopyranosyl)-1-thio-β-D-glycopyranoside 在 三氟化硼乙醚 作用下， 反应 2.0h， 以91%的产率得到phenyl O-<2,3-di-O-benzoyl-4,6-O-<(R)-1-(methoxycarbonyl)ethylidene>-β-D-galactopyranosyl>-(1->4)-2,3,6-tri-O-benzoyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Ziegler, Thomas, Liebigs Annalen, 1995, # 6, p. 949 - 956

  摘要：

  DOI：

文献信息

• Ziegler, Thomas, Liebigs Annalen, 1995, # 6, p. 949 - 956
  作者：Ziegler, Thomas

  DOI：——

  日期：——
• Efficient blockwise synthesis of pyruvated di- and trisaccharide fragments related to Klebsiella K26 capsular polysaccharides
  作者：Thomas Ziegler、Gunter Sch�le

  DOI：10.1002/prac.19963380148

  日期：——

  Pyruvated di- and trisaccharide fragments representing the immunodominant side chains of Klebsiella K26 capsular polysaccharides are prepared. Phenyl 4',6'-O-benzylidene-1-thio-beta-D-lactoside (1) is converted in 4 steps into the corresponding pyruvated 1-thio-lactoside (2) and transformed into the imidate (4). Coupling of the latter with Z-protected 5-aminopentanol gives the pyruvated disaccharide fragment (6) upon deblocking. Similarly, imidate (4) is coupled to allyl 2,3-di-O-benzoyl-3-O-(1-fluoro-1,1,3,3-tetraisopropyl-1,3-disiloxane-3-yl)-alpha-D-glucopyranoside (8) to give the corresponding trisaccharide fragment upon deblocking.