3-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)propanoic acid | 1254963-27-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)propanoic acid
• 英文别名: 3-[(2S,3S,4R,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]propanoic acid
• CAS: 1254963-27-3
• 化学式: C₃₇H₄₀O₇
• 分子量: 596.72
• InChiKey: SIOBNHSBZPHQRM-OJOYEBPYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  44
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-(1-oxybutyric acid methyl ester)-tris[(aminopropoxy)methyl]aminomethane 、 3-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)propanoic acid 在 1-羟基苯并三唑 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以41%的产率得到[Bn4Glu(CH2)2C(O)NH(CH2)3OCH2]3CNHC(O)(CH2)2CO2Me
  参考文献：
  名称：

  Adaptable Synthesis of C-Glycosidic Multivalent Carbohydrates and Succinamide-Linked Derivatization

  摘要：

  A modular approach to the synthesis of trivalent C-glycosidic carbohydrates is described. The approach is illustrated employing carboxylate-terminated C-glycosidic D-mannose, D-glucose, and D-galactose derivatives with different length C1-linked spacer units and also core units with different length linker units attached. The central core scaffold is additionally functionalized via a succinamide-based, conjugatable linker unit, exemplified in an extended multivalent derivative [31] and a pyrene-bearing fluorsecent-labeled tris-C-mannosyl conjugate [33].

  DOI：

  10.1021/ol102310x
• 作为产物：
  描述：

  3-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-1-propanol 在 Jones reagent 作用下， 以 丙酮 为溶剂， 反应 1.75h， 以88%的产率得到3-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)propanoic acid
  参考文献：
  名称：

  Adaptable Synthesis of C-Glycosidic Multivalent Carbohydrates and Succinamide-Linked Derivatization

  摘要：

  A modular approach to the synthesis of trivalent C-glycosidic carbohydrates is described. The approach is illustrated employing carboxylate-terminated C-glycosidic D-mannose, D-glucose, and D-galactose derivatives with different length C1-linked spacer units and also core units with different length linker units attached. The central core scaffold is additionally functionalized via a succinamide-based, conjugatable linker unit, exemplified in an extended multivalent derivative [31] and a pyrene-bearing fluorsecent-labeled tris-C-mannosyl conjugate [33].

  DOI：

  10.1021/ol102310x