methyl 2-O-benzoyl-3,6-di-O-benzyl-4-O-thiocarbonylimidazol-β-D-mannopyranoside | 1152487-22-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-O-benzoyl-3,6-di-O-benzyl-4-O-thiocarbonylimidazol-β-D-mannopyranoside
• CAS: 1152487-22-3
• 化学式: C₃₂H₃₂N₂O₇S
• 分子量: 588.681
• InChiKey: QDGIFCBKSKUTEU-JTODZQAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  42.0
• 可旋转键数：
  11.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  90.27
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  methyl 2-O-benzoyl-3,6-di-O-benzyl-4-O-thiocarbonylimidazol-β-D-mannopyranoside 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 以68%的产率得到methyl 2-O-benzoyl-3,6-di-O-benzyl-4-deoxy-β-D-lyxo-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 configurations of the final deprotected congeners 2-7 were 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 protective epitope recognized by a protective anti-Candida albicans monoclonal antibody C3.1 (IgG3) and to determine its key polar contacts with the binding site. (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.carres.2009.07.008
• 作为产物：
  描述：

  methyl 2-O-benzoyl-3,6-di-O-benzyl-β-D-mannopyranoside 、 N,N'-硫羰基二咪唑 以 甲苯 为溶剂， 反应 20.0h， 以60%的产率得到methyl 2-O-benzoyl-3,6-di-O-benzyl-4-O-thiocarbonylimidazol-β-D-mannopyranoside
  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 configurations of the final deprotected congeners 2-7 were 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 protective epitope recognized by a protective anti-Candida albicans monoclonal antibody C3.1 (IgG3) and to determine its key polar contacts with the binding site. (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.carres.2009.07.008