1,6-anhydro-2,3,5-tri-O-benzoyl-α-D-galactofuranose | 259826-50-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,6-anhydro-2,3,5-tri-O-benzoyl-α-D-galactofuranose
• 英文别名: [(1S,4R,5S,6S,7R)-6,7-dibenzoyloxy-2,8-dioxabicyclo[3.2.1]octan-4-yl] benzoate
• CAS: 259826-50-1
• 化学式: C₂₇H₂₂O₈
• 分子量: 474.467
• InChiKey: FMCHPGHMRFAHGH-PUJHRNRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1,6-anhydro-2,3,5-tri-O-benzoyl-α-D-galactofuranose 在 sodium methylate 作用下， 以 吡啶 、 甲醇 为溶剂， 反应 3.0h， 生成 1,6-anhydro-2,3,5-tri-O-acetyl-α-D-galactofuranose
  参考文献：
  名称：

  An Efficient Method for the Synthesis of A 1,6-Anhydro-α-D-Galactofuranose Derivative and its Application in the Synthesis of Oligosaccharides

  摘要：

  Synthesis of 1,6-anhydro-2,3,5-tri-O-benzoyl-beta-D-galactofuranose (3) has been achieved in good yield by stannic chloride catalysed ring closure of methyl 2,3,4-tri-O-benzoyl-6-O-benzyl-beta-D-galactofuranoside (1). The anhydro compound 3 was converted to the furanoside donors 6 and 7 with an easily removable O-6 acetyl group. The donors 6 and 7 were utilised for the synthesis of a di- and a trisaccharide containing beta-D-galactofuranosides.

  DOI：

  10.1080/07328309908544059
• 作为产物：
  描述：

  methyl 2,3,5-tri-O-benzoyl-α-D-galactofuranose 在 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以79%的产率得到1,6-anhydro-2,3,5-tri-O-benzoyl-α-D-galactofuranose
  参考文献：
  名称：

  An Efficient Method for the Synthesis of A 1,6-Anhydro-α-D-Galactofuranose Derivative and its Application in the Synthesis of Oligosaccharides

  摘要：

  Synthesis of 1,6-anhydro-2,3,5-tri-O-benzoyl-beta-D-galactofuranose (3) has been achieved in good yield by stannic chloride catalysed ring closure of methyl 2,3,4-tri-O-benzoyl-6-O-benzyl-beta-D-galactofuranoside (1). The anhydro compound 3 was converted to the furanoside donors 6 and 7 with an easily removable O-6 acetyl group. The donors 6 and 7 were utilised for the synthesis of a di- and a trisaccharide containing beta-D-galactofuranosides.

  DOI：

  10.1080/07328309908544059

文献信息

• An Efficient Method for the Synthesis of A 1,6-Anhydro-α-D-Galactofuranose Derivative and its Application in the Synthesis of Oligosaccharides
  作者：Sujit Kumar Sarkar、Ambar Kumar Choudhury、Balaram Mukhopadhyay、Nirmolendu Roy

  DOI：10.1080/07328309908544059

  日期：1999.1

  Synthesis of 1,6-anhydro-2,3,5-tri-O-benzoyl-beta-D-galactofuranose (3) has been achieved in good yield by stannic chloride catalysed ring closure of methyl 2,3,4-tri-O-benzoyl-6-O-benzyl-beta-D-galactofuranoside (1). The anhydro compound 3 was converted to the furanoside donors 6 and 7 with an easily removable O-6 acetyl group. The donors 6 and 7 were utilised for the synthesis of a di- and a trisaccharide containing beta-D-galactofuranosides.