3,4,6-tri-O-benzoyl-2-chloro-2-deoxy-α-D-mannopyranosyl chloride | 1542162-38-8

• 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: 3,4,6-tri-O-benzoyl-2-chloro-2-deoxy-α-D-mannopyranosyl chloride
• 英文别名: [(2R,3R,4S,5S,6R)-3,4-dibenzoyloxy-5,6-dichlorooxan-2-yl]methyl benzoate
• CAS: 1542162-38-8
• 化学式: C₂₇H₂₂Cl₂O₇
• 分子量: 529.373
• InChiKey: FMZACOHABPPGGX-HUUMMWPTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3,4,6-三-O-苯甲酰基-D-葡萄糖醛 在 N-氯代丁二酰亚胺 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到3,4,6-tri-O-benzoyl-2-chloro-2-deoxy-α-D-mannopyranosyl chloride
  参考文献：
  名称：

  Highly diastereoselective 1,2-dichlorination of glycals using NCS/PPh3: study of substituent and solvent effects

  摘要：

  Highly diastereoselective 1,2-dichlorination of glycals has been achieved at room temperature conditions in good to excellent yields using a milder, more convenient, less hazardous reagent combination NCS/ PPh3 giving only one major product out of four possible diastereomers [either alpha-gluco (2) or alpha-manno (4)] depending upon the substituents. The diastereoselectivity is maximum (100% alpha/beta-selectivity as well as cis/trans selectivity) for D-galactal and L-rhamnal derivatives. Detailed studies showed that solvent and substituent effects play a significant role in determining the product distribution. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.12.088

文献信息

• Highly diastereoselective 1,2-dichlorination of glycals using NCS/PPh3: study of substituent and solvent effects
  作者：Altaf Hussain、Debaraj Mukherjee

  DOI：10.1016/j.tet.2013.12.088

  日期：2014.2

  Highly diastereoselective 1,2-dichlorination of glycals has been achieved at room temperature conditions in good to excellent yields using a milder, more convenient, less hazardous reagent combination NCS/ PPh3 giving only one major product out of four possible diastereomers [either alpha-gluco (2) or alpha-manno (4)] depending upon the substituents. The diastereoselectivity is maximum (100% alpha/beta-selectivity as well as cis/trans selectivity) for D-galactal and L-rhamnal derivatives. Detailed studies showed that solvent and substituent effects play a significant role in determining the product distribution. (C) 2014 Elsevier Ltd. All rights reserved.