2'-carboxybenzyl (2,3,5-tri-O-benzoyl-6-O-t-butyldimethylsilyl-β-D-galactofuranosyl)-(1->5)-2,3-di-O-benzoyl-6-O-benzyl-β-D-galactofuranoside | 1033706-60-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2'-carboxybenzyl (2,3,5-tri-O-benzoyl-6-O-t-butyldimethylsilyl-β-D-galactofuranosyl)-(1->5)-2,3-di-O-benzoyl-6-O-benzyl-β-D-galactofuranoside
• CAS: 1033706-60-3
• 化学式: C₆₈H₆₈O₁₈Si
• 分子量: 1201.36
• InChiKey: WAKWOJIBCDEIGW-SFJUBYJJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.1
• 重原子数：
  87.0
• 可旋转键数：
  25.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  224.18
• 氢给体数：
  1.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  2'-carboxybenzyl (2,3,5-tri-O-benzoyl-6-O-t-butyldimethylsilyl-β-D-galactofuranosyl)-(1->5)-2,3-di-O-benzoyl-6-O-benzyl-β-D-galactofuranoside 在 2,6-二叔丁基-4-甲基吡啶 、 吡啶 、 三氟甲磺酸酐 、 氢氟酸 、 [双(2-甲氧基乙基)胺]三氟化硫 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 以88%的产率得到(2,3,5-tri-O-benzoyl-6-t-butyldimethylsilyl-β-D-galactofuranosyl)-(1->5)-2,3-di-O-benzoyl-6-O-benzyl-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
• 作为产物：
  描述：

  2'-(benzyloxycarbonyl)benzyl (2,3,5-tri-O-benzoyl-6-O-t-buthyldimethylsilyl-β-D-galactofuranosyl)-(1->5)-2,3-di-O-benzoyl-6-O-benzyl-β-D-galactofuranoside 在 palladium dihydroxide 、 ammonium acetate 、 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 1.0h， 以85%的产率得到2'-carboxybenzyl (2,3,5-tri-O-benzoyl-6-O-t-butyldimethylsilyl-β-D-galactofuranosyl)-(1->5)-2,3-di-O-benzoyl-6-O-benzyl-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