methyl 3,4,6-tri-O-benzyl-β-D-mannopyranosyl-(1->2)-4,6-O-benzylidene-3-O-methyl-β-D-mannopyranoside | 1153910-04-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3,4,6-tri-O-benzyl-β-D-mannopyranosyl-(1->2)-4,6-O-benzylidene-3-O-methyl-β-D-mannopyranoside
• CAS: 1153910-04-3
• 化学式: C₄₂H₄₈O₁₁
• 分子量: 728.837
• InChiKey: SNVCMPZUTGDRCI-LRSWDSDNSA-N

物化性质

• 沸点：
  812.7±65.0 °C(predicted)
• 密度：
  1.28±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

反应信息

• 作为反应物：
  描述：

  methyl 3,4,6-tri-O-benzyl-β-D-mannopyranosyl-(1->2)-4,6-O-benzylidene-3-O-methyl-β-D-mannopyranoside 在 10% Pd on charcoal 、 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以74%的产率得到methyl β-D-mannopyranosyl-(1->2)-3-O-methyl-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 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：

  在 L-Selectride 作用下， 以 四氢呋喃 为溶剂， 以308 mg的产率得到methyl 3,4,6-tri-O-benzyl-β-D-mannopyranosyl-(1->2)-4,6-O-benzylidene-3-O-methyl-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 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