4-methylthiophenyl 2-acetamido-4-S-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3,6-di-O-benzoyl-2-deoxy-1,4-dithio-β-D-glucopyranoside | 1164151-50-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methylthiophenyl 2-acetamido-4-S-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3,6-di-O-benzoyl-2-deoxy-1,4-dithio-β-D-glucopyranoside
• CAS: 1164151-50-1
• 化学式: C₄₃H₄₈N₂O₁₄S₃
• 分子量: 913.057
• InChiKey: RVOPVPCHOGZFLX-FDECSPHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.57
• 重原子数：
  62.0
• 可旋转键数：
  16.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  208.16
• 氢给体数：
  2.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  4-methylthiophenyl 2-acetamido-4-S-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3,6-di-O-benzoyl-2-deoxy-1,4-dithio-β-D-glucopyranoside 在 甲醇 、 sodium methylate 作用下， 反应 16.0h， 以98%的产率得到4-methylthiophenyl 2-acetamido-4-S-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-2-deoxy-1,4-dithio-β-D-glucopyranoside
  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：

  2-乙酰氨基-2-脱氧-1-硫代-beta-D-吡喃葡萄糖 3,4,6-三乙酸酯 、 4-methylthiophenyl 2-acetamido-3,6-di-O-benzoyl-2-deoxy-4-O-trifluormethanesulfonyl-1-thio-β-D-galactopyranoside 在 sodium hydride 、 18-冠醚-6 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 6.08h， 以28%的产率得到4-methylthiophenyl 2-acetamido-4-S-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3,6-di-O-benzoyl-2-deoxy-1,4-dithio-β-D-glucopyranoside
  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