4-methylphenyl 2-acetamido-3,6-di-O-benzoyl-2-deoxy-1-thio-β-D-galactopyranoside | 1164151-33-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methylphenyl 2-acetamido-3,6-di-O-benzoyl-2-deoxy-1-thio-β-D-galactopyranoside
• CAS: 1164151-33-0
• 化学式: C₂₉H₂₉NO₇S
• 分子量: 535.618
• InChiKey: ZWCYZNFKABISTC-KPTFLJRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.76
• 重原子数：
  38.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  111.16
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  三氟甲磺酸酐 、 4-methylphenyl 2-acetamido-3,6-di-O-benzoyl-2-deoxy-1-thio-β-D-galactopyranoside 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以99%的产率得到4-methylphenyl 2-acetamido-3,6-di-O-benzoyl-2-deoxy-4-O-trifluormethane-sulfonyl-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis and conformational analysis of glycomimetic analogs of thiochitobiose

  摘要：

  The synthesis of six analogs of N,N'-diacetylchitobiose is reported, including a novel transglycosylation reaction for the preparation of S-aryl thioglycosides. The conformations of the compounds were studied by a combination of NMR spectroscopy and molecular modeling, using force field calculations. In the case of the S-aryl thioglycosides with exclusively S-glycosidic linkages, dihedral angles of the disaccharidic S-glycosidic bonds, Phi' and Psi' and of the S-arylglycoside bonds, Phi and Psi, were found to be similar, whereas they were different in mixed glycosides and in a thiazoline derivative. An adequate correlation between the calculated H,H-distances of the local minima and the measured NOE contacts was achieved by applying population-weighted averages over participating conformers based on weighted relative energies. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.03.067
• 作为产物：
  描述：

  4-methylphenyl 2-acetamido-4-O-acetyl-3,6-di-O-benzoyl-2-deoxy-1-thio-β-D-galactopyranoside 在 甲醇 、 乙酰氯 作用下， 以 氯仿 为溶剂， 以16.7%的产率得到4-methylphenyl 2-acetamido-3,6-di-O-benzoyl-2-deoxy-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis and conformational analysis of glycomimetic analogs of thiochitobiose

  摘要：

  The synthesis of six analogs of N,N'-diacetylchitobiose is reported, including a novel transglycosylation reaction for the preparation of S-aryl thioglycosides. The conformations of the compounds were studied by a combination of NMR spectroscopy and molecular modeling, using force field calculations. In the case of the S-aryl thioglycosides with exclusively S-glycosidic linkages, dihedral angles of the disaccharidic S-glycosidic bonds, Phi' and Psi' and of the S-arylglycoside bonds, Phi and Psi, were found to be similar, whereas they were different in mixed glycosides and in a thiazoline derivative. An adequate correlation between the calculated H,H-distances of the local minima and the measured NOE contacts was achieved by applying population-weighted averages over participating conformers based on weighted relative energies. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.03.067