benzyl 3-O-benzyl-2-deoxy-4-O-(4,6-di-O-acetyl-2,3-O-carbonyl-β-D-mannopyranosyl)-L-erythro-pentopyranoside | 136737-34-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 3-O-benzyl-2-deoxy-4-O-(4,6-di-O-acetyl-2,3-O-carbonyl-β-D-mannopyranosyl)-L-erythro-pentopyranoside
• CAS: 136737-34-3
• 化学式: C₃₀H₃₄O₁₂
• 分子量: 586.593
• InChiKey: YXXWIFQUOSNBKA-BHIVIROESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.04
• 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：
  0.5
• 拓扑面积：
  134.28
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  benzyl 3-O-benzyl-2-deoxy-4-O-(4,6-di-O-acetyl-2,3-O-carbonyl-β-D-mannopyranosyl)-L-erythro-pentopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以96%的产率得到benzyl 3-O-benzyl-2-deoxy-4-O-β-D-mannopyranosyl-β-L-erythro-pentopyranoside
  参考文献：
  名称：

  Synthesis of 2-deoxy-4- O -α- and -β- d -mannopyransyl- l - erythro -pentonic acids

  摘要：

  The title compounds, required for the identification of structural features of the Bordetella pertussis endotoxin, have been synthesised by condensation of benzyl 3-O-benzyl-2-deoxy-beta-L-erythro-pentopyranoside with 2,3,4,6-tetra-O-benzoyl-alpha-D-mannopyranosyl bromide and with 4,6-di-O-acetyl-2,3-O-carbonyl-alpha-D-mannopyranosyl bromide, respectively, thus affording the fully protected alpha- and beta-linked disaccharides 7 and 12. Hypoiodite oxidation of the reducing disaccharides 9 and 14, obtained by conventional deprotection of 7 and 12, yielded the title compounds.

  DOI：

  10.1016/0008-6215(92)84164-n
• 作为产物：
  描述：

  benzyl 2-deoxy-β-L-erythro-pentopyranoside 在 calcium sulfate 、 四丁基溴化铵 、 二正丁基氧化锡 、 silver(l) oxide 作用下， 反应 21.5h， 生成 benzyl 3-O-benzyl-2-deoxy-4-O-(4,6-di-O-acetyl-2,3-O-carbonyl-β-D-mannopyranosyl)-L-erythro-pentopyranoside
  参考文献：
  名称：

  Synthesis of 2-deoxy-4- O -α- and -β- d -mannopyransyl- l - erythro -pentonic acids

  摘要：

  The title compounds, required for the identification of structural features of the Bordetella pertussis endotoxin, have been synthesised by condensation of benzyl 3-O-benzyl-2-deoxy-beta-L-erythro-pentopyranoside with 2,3,4,6-tetra-O-benzoyl-alpha-D-mannopyranosyl bromide and with 4,6-di-O-acetyl-2,3-O-carbonyl-alpha-D-mannopyranosyl bromide, respectively, thus affording the fully protected alpha- and beta-linked disaccharides 7 and 12. Hypoiodite oxidation of the reducing disaccharides 9 and 14, obtained by conventional deprotection of 7 and 12, yielded the title compounds.

  DOI：

  10.1016/0008-6215(92)84164-n