1,4-anhydro-2,3,6-tri-O-benzoyl-β-D-galactopyranose | 56933-10-9

• 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: 1,4-anhydro-2,3,6-tri-O-benzoyl-β-D-galactopyranose
• 英文别名: [(1S,3R,4S,5S,6R)-5,6-dibenzoyloxy-2,7-dioxabicyclo[2.2.1]heptan-3-yl]methyl benzoate
• CAS: 56933-10-9
• 化学式: C₂₇H₂₂O₈
• 分子量: 474.467
• InChiKey: XRUBQRSQAFJMOQ-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：
  10
• 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

• 作为产物：
  描述：

  2,3,6-tri-O-benzoyl-α-D-galactopyranosyl fluoride 在 3 A molecular sieve 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以47%的产率得到1,4-anhydro-2,3,6-tri-O-benzoyl-β-D-galactopyranose
  参考文献：
  名称：

  Preparations and reactions of acylated and partially acylated glycosyl fluorides

  摘要：

  Partial acylation of glycosyl fluorides in the galacto (2 and 3) and gluco series (8-10) is readily achieved. Attempts to further alkylate these acyl derivatives failed. Treatment of 2 with Lewis acid, however, provided a facile route to the 1,4-anhydro derivative 5. Lewis acid-mediated glycosylation of 2-acetamido-3,4,6-tri-O-acetyl-alpha-D-glucopyranosyl fluoride 11 led to the simple glycosides and thioglycosides 12-16. Similarly, in the galacto series (17) an advantageous route to the beta-galactosidase inhibitor 19 could be elaborated.

  DOI：

  10.1016/0008-6215(93)84069-i

文献信息

• A novel route to 1,4-anhydro derivatives of β-d-galactopyranose
  作者：Clive Bullock、Leslie Hough、Anthony C. Richardson

  DOI：10.1016/0008-6215(90)84136-i

  日期：1990.3
• BULLOCK, CLIVE;HOUGH, LESLIE;RICHARDSON, ANTHONY C., CARBOHYDR. RES., 197,(1990) C. 131-138
  作者：BULLOCK, CLIVE、HOUGH, LESLIE、RICHARDSON, ANTHONY C.

  DOI：——

  日期：——