4-methylphenyl 2-acetamido-4-S-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-2-deoxy-1,4-dithio-β-D-glucopyranoside | 1164151-21-6

• 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-4-S-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-2-deoxy-1,4-dithio-β-D-glucopyranoside
• 英文别名: N-[(2S,3R,4R,5S,6R)-2-[(2R,3S,4R,5R,6S)-5-acetamido-4-hydroxy-2-(hydroxymethyl)-6-(4-methylphenyl)sulfanyloxan-3-yl]sulfanyl-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• CAS: 1164151-21-6
• 化学式: C₂₃H₃₄N₂O₉S₂
• 分子量: 546.663
• InChiKey: BGNMQULJWKXEFM-AYDAZSPTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  228
• 氢给体数：
  7
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  4-methylphenyl 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95%的产率得到4-methylphenyl 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

文献信息

• Synthesis and conformational analysis of glycomimetic analogs of thiochitobiose
  作者：Anja Fettke、Dirk Peikow、Martin G. Peter、Erich Kleinpeter

  DOI：10.1016/j.tet.2009.03.067

  日期：2009.5

  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.