2-methyl-4-S-[(3,4,6-tri-O-acetyl-2-deoxy-2-thioacetamido-β-D-glucopyranosyl)]-(3,6-di-O-benzoyl-1,2-dideoxy-α-D-glucopyrano)-[2,1-d]-2-thiazoline | 1164151-57-8

• 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-methyl-4-S-[(3,4,6-tri-O-acetyl-2-deoxy-2-thioacetamido-β-D-glucopyranosyl)]-(3,6-di-O-benzoyl-1,2-dideoxy-α-D-glucopyrano)-[2,1-d]-2-thiazoline
• CAS: 1164151-57-8
• 化学式: C₃₆H₄₀N₂O₁₂S₃
• 分子量: 788.918
• InChiKey: FAPKQNGCIRYHKS-CIUJPUOKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.89
• 重原子数：
  53.0
• 可旋转键数：
  12.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  174.35
• 氢给体数：
  1.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  2-methyl-4-S-[(3,4,6-tri-O-acetyl-2-deoxy-2-thioacetamido-β-D-glucopyranosyl)]-(3,6-di-O-benzoyl-1,2-dideoxy-α-D-glucopyrano)-[2,1-d]-2-thiazoline 在 甲醇 、 sodium methylate 作用下， 反应 16.0h， 以98%的产率得到2-methyl 4-S-[(2-deoxy-2-thioacetamido-β-D-glucopyranosyl)]-(1,2-dideoxy-α-D-glucopyrano)-[2,1-d]-2-thiazoline
  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-methoxyphenyl 2-acetamido-4-S-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-gluco-pyranosyl)-3,6-di-O-benzoyl-2-deoxy-4-thio-β-D-glucopyranoside 在 劳森试剂 作用下， 以 甲苯 为溶剂， 反应 72.0h， 以56%的产率得到2-methyl-4-S-[(3,4,6-tri-O-acetyl-2-deoxy-2-thioacetamido-β-D-glucopyranosyl)]-(3,6-di-O-benzoyl-1,2-dideoxy-α-D-glucopyrano)-[2,1-d]-2-thiazoline
  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