3,4,6-tri-O-benzyl-2-chloro-2-deoxy-α-D-glucopyranosyl chloride | 62098-45-7

• 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-benzyl-2-chloro-2-deoxy-α-D-glucopyranosyl chloride
• 英文别名: 3,4,6-Tri-O-benzyl-2-chloro-2-desoxy-α-D-glucopyranosylchlorid；(2R,3R,4S,5R,6R)-2,3-dichloro-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
• CAS: 62098-45-7
• 化学式: C₂₇H₂₈Cl₂O₄
• 分子量: 487.423
• InChiKey: QJZVVAQCRPSRPA-ACFIUOAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3,4,6-三苄氧基-D-葡萄烯糖 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62%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

文献信息

• The lithiation of 2-chloroglucal derivatives
  作者：Ewan Boyd、Michael R. Hallett、Ray V.H. Jones、James E. Painter、Prakash Patel、Peter Quayle、Anita J. Waring (née Potts)

  DOI：10.1016/j.tetlet.2006.09.087

  日期：2006.11

  Lithiation of 2-chloroglucal derivatives provides ready access to the corresponding 1-lithioglucals which undergo a variety of serve useful intermediates for further elaboration of the carbohydrate nucleus. Removal of the 2-chloro substituent may be affected using a Birch-type reduction. (c) 2006 Elsevier Ltd. All rights reserved.