(2,3-di-O-benzoyl-6-O-benzyl-β-D-galactofuranosyl)-(1->6)-2,3,5-tri-O-benzoyl-β-D-galactofuranosyl fluoride | 1033706-95-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2,3-di-O-benzoyl-6-O-benzyl-β-D-galactofuranosyl)-(1->6)-2,3,5-tri-O-benzoyl-β-D-galactofuranosyl fluoride
• 英文别名: Bz(-2)[Bz(-3)][Bn(-6)]Galf(b1-6)[Bz(-2)][Bz(-3)][Bz(-5)]b-Galf1F；[(2S,3S,4R,5R)-4-benzoyloxy-5-[(2R)-2-benzoyloxy-2-[(2S,3S,4R,5S)-3,4-dibenzoyloxy-5-fluorooxolan-2-yl]ethoxy]-2-[(1R)-1-hydroxy-2-phenylmethoxyethyl]oxolan-3-yl] benzoate
• CAS: 1033706-95-4
• 化学式: C₅₄H₄₇FO₁₅
• 分子量: 954.957
• InChiKey: CLDFGXJHGLJXCI-IHQKEAPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  70
• 可旋转键数：
  24
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  189
• 氢给体数：
  1
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  (2,3-di-O-benzoyl-6-O-benzyl-β-D-galactofuranosyl)-(1->6)-2,3,5-tri-O-benzoyl-β-D-galactofuranosyl fluoride 在 silver perchlorate 、 tin(ll) chloride 作用下， 以 乙醚 为溶剂， 以32%的产率得到cyclo-[5-(2,3-di-O-benzoyl-6-O-benzyl-β-D-galactofuranosyl)-(1->6)-(2,3,5-tri-O-benzoyl-β-D-galactofuranosyl)-1->]3
  参考文献：
  名称：

  Chemical Synthesis of Cyclic Galactooligofuranosides Isolated from Enzymatic Degradation Products of Cell Wall Arabinogalactan of Mycobacterium tuberculosis

  摘要：

  Synthesis of cyclic tetra-, hexa- and octasaccharides containing alternating (1 -> 5)-,beta- and (1 -> 6)-beta-galactofuranosyl linkages has been achieved by intramolecular cycloglycosylation of corresponding linear sugars and by cyclooligomerization of 1,6-linked and 1,5-linked disaccharides. In particular,cyclooligornerization of the (1 -> 6)-beta-galactofuranosyl disaccharide provides an efficient way to secure all three cyclic sugars in one operation.

  DOI：

  10.1021/ol800530u
• 作为产物：
  描述：

  (2,3-di-O-benzoyl-6-O-benzyl-5-O-levulinyl-β-D-galactofuranosyl)-(1->6)-2,3,5-tri-O-benzoyl-β-D-galactofuranosyl fluoride 在 溶剂黄146 、 肼 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.5h， 以89%的产率得到(2,3-di-O-benzoyl-6-O-benzyl-β-D-galactofuranosyl)-(1->6)-2,3,5-tri-O-benzoyl-β-D-galactofuranosyl fluoride
  参考文献：
  名称：

  Chemical Synthesis of Cyclic Galactooligofuranosides Isolated from Enzymatic Degradation Products of Cell Wall Arabinogalactan of Mycobacterium tuberculosis

  摘要：

  Synthesis of cyclic tetra-, hexa- and octasaccharides containing alternating (1 -> 5)-,beta- and (1 -> 6)-beta-galactofuranosyl linkages has been achieved by intramolecular cycloglycosylation of corresponding linear sugars and by cyclooligomerization of 1,6-linked and 1,5-linked disaccharides. In particular,cyclooligornerization of the (1 -> 6)-beta-galactofuranosyl disaccharide provides an efficient way to secure all three cyclic sugars in one operation.

  DOI：

  10.1021/ol800530u