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 | 177356-13-7

• 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: 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
• CAS: 177356-13-7
• 化学式: C₆₄H₆₃NO₂₀
• 分子量: 1166.2
• InChiKey: RVFQXESLJWYVCL-UHLVBUPHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.0
• 重原子数：
  85.0
• 可旋转键数：
  23.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  251.51
• 氢给体数：
  1.0
• 氢受体数：
  20.0

反应信息

• 作为反应物：
  描述：

  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 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 (2R,4aR,6S,7R,8R,8aR)-6-[(2R,3S,4R,5R,6R)-6-(5-Benzyloxycarbonylamino-pentyloxy)-4,5-dihydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy]-7,8-dihydroxy-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxine-2-carboxylic acid methyl ester
  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：

  O-<2,3-di-O-benzoyl-4,6-O-<(R)-1-methoxycarbonyl(ethylidene)>-β-D-galactopyranosyl>-(1->4)-2,3,6-tri-O-benzoyl-D-glucopyranose 在 三氟化硼乙醚 、 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 24.33h， 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