2'-(benzyloxycarbonyl)benzyl 2,3,5-tri-O-benzoyl-β-D-galactofuranoside | 1033706-52-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2'-(benzyloxycarbonyl)benzyl 2,3,5-tri-O-benzoyl-β-D-galactofuranoside
• CAS: 1033706-52-3
• 化学式: C₄₂H₃₆O₁₁
• 分子量: 716.741
• InChiKey: KJIANPXDNNOADX-FIGOLCKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.95
• 重原子数：
  53.0
• 可旋转键数：
  14.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  143.89
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  2'-(benzyloxycarbonyl)benzyl 2,3,5-tri-O-benzoyl-β-D-galactofuranoside 、 2'-carbonylbenzyl 2,3-di-O-benzoyl-6-O-benzyl-5-O-levulinyl-β-D-galactofuranoside 在 2,6-二叔丁基-4-甲基吡啶 、 三氟甲磺酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以72%的产率得到2'-(benzyloxycarbonyl)benzyl (2,3-di-O-benzoyl-6-O-benzyl-5-O-levulinyl-β-D-galactofuranosyl)-(1->6)-2,3,5-tri-O-benzoyl-β-D-galactofuranoside
  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'-(benzyloxycarbonyl)benzyl 2,3,5-tri-O-benzoyl-6-O-t-butyldimethylsilyl-β-D-galactofuranoside 在 吡啶 、 氢氟酸 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以96%的产率得到2'-(benzyloxycarbonyl)benzyl 2,3,5-tri-O-benzoyl-β-D-galactofuranoside
  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