methyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl-(1->2)-4,6-O-benzylidene-3-deoxy-β-D-arabino-hexopyranoside | 1152487-07-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl-(1->2)-4,6-O-benzylidene-3-deoxy-β-D-arabino-hexopyranoside
• CAS: 1152487-07-4
• 化学式: C₄₃H₄₈O₁₁
• 分子量: 740.848
• InChiKey: YOXIXXUNPJVQTF-OPSMIVNOSA-N

物化性质

• 沸点：
  798.9±60.0 °C(predicted)
• 密度：
  1.27±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.29
• 重原子数：
  54.0
• 可旋转键数：
  15.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  109.37
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  methyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl-(1->2)-4,6-O-benzylidene-3-deoxy-β-D-arabino-hexopyranoside 在 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 以166 mg的产率得到methyl 3,4,6-tri-O-benzyl-β-D-glucopyranosyl-(1->2)-4,6-O-benzylidene-3-deoxy-β-D-arabino-hexopyranoside
  参考文献：
  名称：

  Synthesis of monodeoxy and mono-O-methyl congeners of methyl β-d-mannopyranosyl-(1→2)-β-d-mannopyranoside for epitope mapping of anti-Candida albicans antibodies

  摘要：

  A panel of six complementary monodeoxy and mono-O-methyl congeners of methyl beta-D-mannopyranosyl-(1 -> 2)-beta-D-mannopyranoside (1) were synthesized by stereoselective glycosylation of monodeoxy and mono-O-methyl monosaccharide acceptors with a 2-O-acetyl-glucosyl trichloroacetimidate donor, followed by a two-step oxidation-reduction sequence at C-2'. The beta-manno configuration of the final deprotected congeners 2-7 was confirmed by measurement of (1)J(C1.H1) heteronuclear and (3)J(1'.2), homonuclear coupling constants. These disaccharide derivatives will be used to map the epitope recognized bit a protective anti-Candida albicans monoclonal antibody C3.1 (IgG3) and to determine its key polar contacts with the binding site. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.12.011
• 作为产物：
  描述：

  methyl 4,6-O-benzylidene-3-deoxy-β-D-arabino-hexopyranoside 、 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 以59%的产率得到methyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl-(1->2)-4,6-O-benzylidene-3-deoxy-β-D-arabino-hexopyranoside
  参考文献：
  名称：

  Synthesis of monodeoxy and mono-O-methyl congeners of methyl β-d-mannopyranosyl-(1→2)-β-d-mannopyranoside for epitope mapping of anti-Candida albicans antibodies

  摘要：

  A panel of six complementary monodeoxy and mono-O-methyl congeners of methyl beta-D-mannopyranosyl-(1 -> 2)-beta-D-mannopyranoside (1) were synthesized by stereoselective glycosylation of monodeoxy and mono-O-methyl monosaccharide acceptors with a 2-O-acetyl-glucosyl trichloroacetimidate donor, followed by a two-step oxidation-reduction sequence at C-2'. The beta-manno configuration of the final deprotected congeners 2-7 was confirmed by measurement of (1)J(C1.H1) heteronuclear and (3)J(1'.2), homonuclear coupling constants. These disaccharide derivatives will be used to map the epitope recognized bit a protective anti-Candida albicans monoclonal antibody C3.1 (IgG3) and to determine its key polar contacts with the binding site. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.12.011