octyl 5-azido-5-deoxy-α-D-arabinofuranosyl-(1->3)-[5-azido-5-deoxy-α-D-arabinofuranosyl-(1->5)]-α-D-arabinofuranoside | 685111-60-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: octyl 5-azido-5-deoxy-α-D-arabinofuranosyl-(1->3)-[5-azido-5-deoxy-α-D-arabinofuranosyl-(1->5)]-α-D-arabinofuranoside
• 英文别名: (2R,3S,4S,5S)-2-(azidomethyl)-5-[[(2R,3S,4S,5S)-3-[(2R,3S,4S,5R)-5-(azidomethyl)-3,4-dihydroxyoxolan-2-yl]oxy-4-hydroxy-5-octoxyoxolan-2-yl]methoxy]oxolane-3,4-diol
• CAS: 685111-60-8
• 化学式: C₂₃H₄₀N₆O₁₁
• 分子量: 576.604
• InChiKey: BYAUASHXOPSWLI-TVQQQLAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  40
• 可旋转键数：
  17
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  185
• 氢给体数：
  5
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  octyl 5-azido-5-deoxy-α-D-arabinofuranosyl-(1->3)-[5-azido-5-deoxy-α-D-arabinofuranosyl-(1->5)]-α-D-arabinofuranoside 在 水 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以83%的产率得到octyl 5-amino-5-deoxy-α-D-arabinofuranosyl-(1->3)-[5-amino-5-deoxy-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：

  octyl 2-O-benzoyl-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-azido-5-deoxy-α-D-arabinofuranosyl-(1->3)-[5-azido-5-deoxy-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

文献信息

• Synthesis of oligosaccharides as potential inhibitors of mycobacterial arabinosyltransferases. Di- and trisaccharides containing C-5 modified arabinofuranosyl residues
  作者：Oana M. Cociorva、Todd L. Lowary

  DOI：10.1016/j.carres.2003.12.015

  日期：2004.3

  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.