p-toluyl 2,3-di-O-benzoyl-5-O-methyl-1-thio-α-D-arabinofuranoside | 685111-64-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-toluyl 2,3-di-O-benzoyl-5-O-methyl-1-thio-α-D-arabinofuranoside
• CAS: 685111-64-2
• 化学式: C₂₇H₂₆O₆S
• 分子量: 478.566
• InChiKey: XKFFQZRIYTWNOL-CHQSNSNVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.91
• 重原子数：
  34.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  71.06
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  p-toluyl 2,3-di-O-benzoyl-5-O-methyl-1-thio-α-D-arabinofuranoside 在 N-碘代丁二酰亚胺 、 sodium methylate 、 silver trifluoromethanesulfonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.08h， 生成 octyl 5-O-methyl-α-D-arabinofuranosyl-(1->3)-[5-O-methyl-α-D-arabinofuranosyl-(1->5)]-α-D-arabinofuranoside
  参考文献：
  名称：

  Synthesis of oligosaccharides as potential inhibitors of mycobacterial arabinosyltransferases. Di- and trisaccharides containing C-5 modified arabinofuranosyl residues

  摘要：

  The synthesis of a panel of oligosaccharides containing C-5 arabinofuranosyl residues (9-20) is described. These compounds are of interest as potential inhibitors of the alpha-(I --> 5)-arabinosyltransferase involved in the assembly of mycobacterial cell-wall arabinan. In the series of compounds prepared, the 5-OH group on the nonreducing residue(s) is replaced, independently, with an amino, azido. fluoro, or methoxy functionality. The synthesis of the target compounds involved the preparation of a series of C-5 modified arabinofuranosyl thioglycosides (24-26) and their subsequent coupling to the appropriate acceptor species (21-23). Deprotection of the glycosylation products afforded the azido, fluoro, or methoxy analogs directly. The amino derivatives were obtained in one additional step by reduction of the azido compounds. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2003.12.015
• 作为产物：
  描述：

  p-toluyl 2,3-di-O-benzoyl-5-O-triphenylmethyl-1-thio-α-D-arabinofuranoside 在 tetrafluoroboric acid 、 对甲苯磺酸 作用下， 以 甲醇 、 正己烷 、 二氯甲烷 、 水 为溶剂， 反应 1.83h， 生成 p-toluyl 2,3-di-O-benzoyl-5-O-methyl-1-thio-α-D-arabinofuranoside
  参考文献：
  名称：

  Synthesis of oligosaccharides as potential inhibitors of mycobacterial arabinosyltransferases. Di- and trisaccharides containing C-5 modified arabinofuranosyl residues

  摘要：

  The synthesis of a panel of oligosaccharides containing C-5 arabinofuranosyl residues (9-20) is described. These compounds are of interest as potential inhibitors of the alpha-(I --> 5)-arabinosyltransferase involved in the assembly of mycobacterial cell-wall arabinan. In the series of compounds prepared, the 5-OH group on the nonreducing residue(s) is replaced, independently, with an amino, azido. fluoro, or methoxy functionality. The synthesis of the target compounds involved the preparation of a series of C-5 modified arabinofuranosyl thioglycosides (24-26) and their subsequent coupling to the appropriate acceptor species (21-23). Deprotection of the glycosylation products afforded the azido, fluoro, or methoxy analogs directly. The amino derivatives were obtained in one additional step by reduction of the azido compounds. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2003.12.015