octyl 5-O-(5-deoxy-5-azido-α-D-arabinofuranosyl)-α-D-arabinofuranoside | 651706-62-6

• 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-O-(5-deoxy-5-azido-α-D-arabinofuranosyl)-α-D-arabinofuranoside
• 英文别名: octyl 5-azido-5-deoxy-α-D-arabinofuranosyl-(1->5)-α-D-arabinofuranoside；(2R,3S,4S,5S)-2-(azidomethyl)-5-[[(2R,3S,4S,5S)-3,4-dihydroxy-5-octoxy-tetrahydrofuran-2-yl]methoxy]tetrahydrofuran-3,4-diol；(2R,3S,4S,5S)-2-(azidomethyl)-5-[[(2R,3S,4S,5S)-3,4-dihydroxy-5-octoxyoxolan-2-yl]methoxy]oxolane-3,4-diol
• CAS: 651706-62-6
• 化学式: C₁₈H₃₃N₃O₈
• 分子量: 419.475
• InChiKey: PIMGNJQSRGIVHB-MSGXSSGNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  29
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  132
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  octyl 5-O-(5-deoxy-5-azido-α-D-arabinofuranosyl)-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73%的产率得到octyl 5-O-(5-deoxy-5-amino-α-D-arabinofuranosyl)-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-tolyl 1-thio-α-D-arabinofuranoside 在 吡啶 、 4-二甲氨基吡啶 、 N-碘代丁二酰亚胺 、 sodium azide 、 18-冠醚-6 、 sodium methylate 、 silver trifluoromethanesulfonate 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.08h， 生成 octyl 5-O-(5-deoxy-5-azido-α-D-arabinofuranosyl)-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

• Arabinofuranose disaccharide analogs as inhibitors of Mycobacterium tuberculosis
  作者：Ashish K Pathak、Vibha Pathak、Manish Kulshrestha、Darren Kinnaird、William J Suling、S.S Gurcha、Gurdyal S Besra、Robert C Reynolds

  DOI：10.1016/j.tet.2003.10.054

  日期：2003.12

  noside disaccharide analogs substituted at the 5-position of the non-reducing end sugar were synthesized and tested in vitro against Mycobacterium tuberculosis (M.tb.), Mycobacterium avium complex (MAC) as well as in a cell free assay system for arabinosyltransferase acceptor/inhibitor activity. A few compounds showed interesting inhibitory activity in the cell free assay as well as against the whole

  合成了在非还原性末端糖的5位上取代的几个5 - O-（α-d-阿拉伯呋喃糖基）-α-d-呋喃糖苷二糖类似物，并在体外针对结核分枝杆菌（M.tb.）进行了测试，鸟分枝杆菌复合物（MAC）以及无细胞分析系统中的阿拉伯糖基转移酶受体/抑制剂活性。一些化合物在无细胞测定以及体外对整个微生物的抑制作用中均表现出令人感兴趣的效果。
• 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.