phenyl 6-O-methyl-2,3-di-O-pentyl-1-thio-β-D-glucopyranose | 322472-92-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 6-O-methyl-2,3-di-O-pentyl-1-thio-β-D-glucopyranose
• 英文别名: (2R,3R,4S,5R,6S)-2-(methoxymethyl)-4,5-dipentoxy-6-phenylsulfanyloxan-3-ol
• CAS: 322472-92-4
• 化学式: C₂₃H₃₈O₅S
• 分子量: 426.618
• InChiKey: CXZOCNPQNNRXFL-ZQGJOIPISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  29
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  82.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  苯基-4,6-O-苯亚甲基-1-硫代-Β-D-吡喃葡萄糖苷 在 sodium hydroxide 、 lithium aluminium tetrahydride 、 三氯化铝 、 三氯化铁 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 11.75h， 生成 phenyl 6-O-methyl-2,3-di-O-pentyl-1-thio-β-D-glucopyranose
  参考文献：
  名称：

  General access to asymmetric γ-cyclodextrins for gas chromatographic applications by insertion of a selectively modified sugar unit

  摘要：

  Gas chromatography (GC) using chiral stationary phases (CSPs) based on modified cyclodextrins is the most commonly used technique to quantify enantiomeric purity of synthesized volatile racemic drugs. The fully methylated cyclodextrin derivatives are the most used because of their easy synthesis, their thermal stability and their ability to recognize a wide range of compounds. To complete the background on molecular recognition, we describe a route to access fully characterized new asymmetric cyclodextrins derived from fully methylated ones, thereby directly useful in chiral gas chromatography. The synthesis of these compounds involves a three-step procedure: ring opening of fully methylated cyclodextrins, elongation of the chain with correctly modified monosaccharide derivatives and, finally, macrocyclization to obtain the desired compounds. This strategy is applied to achieve the synthesis of a series of asymmetric gamma -cyclodextrins, by insertion of glucopyranosic derivatives. Appropriate selection of the glycosylating reagents during chain elongation and macrocyclization steps allows satisfactory anomeric selectivities to be reached. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00396-7

文献信息

• General access to asymmetric γ-cyclodextrins for gas chromatographic applications by insertion of a selectively modified sugar unit
  作者：Eric Bourgeaux、Jean-Claude Combret

  DOI：10.1016/s0957-4166(00)00396-7

  日期：2000.10

  Gas chromatography (GC) using chiral stationary phases (CSPs) based on modified cyclodextrins is the most commonly used technique to quantify enantiomeric purity of synthesized volatile racemic drugs. The fully methylated cyclodextrin derivatives are the most used because of their easy synthesis, their thermal stability and their ability to recognize a wide range of compounds. To complete the background on molecular recognition, we describe a route to access fully characterized new asymmetric cyclodextrins derived from fully methylated ones, thereby directly useful in chiral gas chromatography. The synthesis of these compounds involves a three-step procedure: ring opening of fully methylated cyclodextrins, elongation of the chain with correctly modified monosaccharide derivatives and, finally, macrocyclization to obtain the desired compounds. This strategy is applied to achieve the synthesis of a series of asymmetric gamma -cyclodextrins, by insertion of glucopyranosic derivatives. Appropriate selection of the glycosylating reagents during chain elongation and macrocyclization steps allows satisfactory anomeric selectivities to be reached. (C) 2000 Elsevier Science Ltd. All rights reserved.