benzyl 2,3-di-O-benzyl-6-O-benzoyl-β-D-galactopyranoside | 313352-43-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 2,3-di-O-benzyl-6-O-benzoyl-β-D-galactopyranoside
• 英文别名: [(2R,3S,4S,5R,6R)-3-hydroxy-4,5,6-tris(phenylmethoxy)oxan-2-yl]methyl benzoate
• CAS: 313352-43-1
• 化学式: C₃₄H₃₄O₇
• 分子量: 554.64
• InChiKey: QMSUAHOWIOAMNA-BWMDDLPLSA-N

物化性质

• 熔点：
  94-96°C
• 沸点：
  687.0±55.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于可溶于丙酮、可溶于氯仿、二氯甲烷

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  41
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 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：

  benzyl 2,3-di-O-benzyl-6-O-benzoyl-β-D-galactopyranoside 、 ethyl 2-O-acetyl-3,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 作用下， 以 甲苯 、 二氯甲烷 为溶剂， 以75%的产率得到benzyl 2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranosyl-(1>4)-2,3-di-O-benzyl-6-O-benzoyl-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis and Solution-Phase Conformation of the RG-I Fragment of the Plant Polysaccharide Pectin Reveals a Modification-Modulated Assembly Mechanism

  摘要：

  The syntheses of pure RG-I fragments of key plant matrix biomolecule pectin using a counterintuitive late-stage convergent cis-glycosylation has allowed detailed analyses of their solution-phase conformations, metal binding affinities, pK(a) values, self-assembly equilibria, and diffusional kinetics. These reveal a striking, right-handed 3(1)-helix that provides an effective and repeating lateral display of putative liganding carboxylates. Moreover, these heteropolymeric structures allow units as short as tetrasaccharides to self-assemble through carbohydrate-carbohydrate interactions that are induced by the presence of Ca(II), a known dynamic trigger in planta. These self-assembly properties can be switched simply by the addition or removal of a single methyl group in this repeating unit through methyl (de)esterification, another known dynamic trigger in planta. Together, the combined effect of Ca(II) and methylation revealed here suggests a concerted molecular basis for these two major dynamic modifications in planta.

  DOI：

  10.1021/ja9090963

文献信息

• Synthesis and Solution-Phase Conformation of the RG-I Fragment of the Plant Polysaccharide Pectin Reveals a Modification-Modulated Assembly Mechanism
  作者：Eoin M. Scanlan、Mukram M. Mackeen、Mark R. Wormald、Benjamin G. Davis

  DOI：10.1021/ja9090963

  日期：2010.6.2

  The syntheses of pure RG-I fragments of key plant matrix biomolecule pectin using a counterintuitive late-stage convergent cis-glycosylation has allowed detailed analyses of their solution-phase conformations, metal binding affinities, pK(a) values, self-assembly equilibria, and diffusional kinetics. These reveal a striking, right-handed 3(1)-helix that provides an effective and repeating lateral display of putative liganding carboxylates. Moreover, these heteropolymeric structures allow units as short as tetrasaccharides to self-assemble through carbohydrate-carbohydrate interactions that are induced by the presence of Ca(II), a known dynamic trigger in planta. These self-assembly properties can be switched simply by the addition or removal of a single methyl group in this repeating unit through methyl (de)esterification, another known dynamic trigger in planta. Together, the combined effect of Ca(II) and methylation revealed here suggests a concerted molecular basis for these two major dynamic modifications in planta.