2,3,4,6-tetra-O-acetyl-2-chloro-α-D-glucopyranosyl chloride | 1542162-39-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2,3,4,6-tetra-O-acetyl-2-chloro-α-D-glucopyranosyl chloride
• 英文别名: [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-5,6-dichlorooxan-2-yl]methyl acetate
• CAS: 1542162-39-9
• 化学式: C₁₄H₁₈Cl₂O₉
• 分子量: 401.198
• InChiKey: FHTRKVORPBDBST-DGTMBMJNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  [(2R,3R,4S)-4,5-二乙酰氧基-2-(乙酰氧基甲基)-3,4-二氢-2H-吡喃-3-基]乙酸酯 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52%的产率得到
  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