octyl 2,5-di-O-benzoyl-α-D-arabinofuranoside | 569659-32-1

• 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 2,5-di-O-benzoyl-α-D-arabinofuranoside
• 英文别名: [(2R,3R,4S,5S)-4-benzoyloxy-3-hydroxy-5-octoxyoxolan-2-yl]methyl benzoate
• CAS: 569659-32-1
• 化学式: C₂₇H₃₄O₇
• 分子量: 470.563
• InChiKey: FMRPMTZHCZBWSA-INADMSBESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  34
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  91.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  octyl 2,5-di-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 0.17h， 生成 octyl 3-O-(2,3-anhydro-α-D-ribofuranosyl)-α-D-arabinofuranoside
  参考文献：
  名称：

  2,3-脱水糖在糖苷键合成中的作用。在制备C-2功能化的α-d-阿拉伯呋喃糖苷中的应用

  摘要：

  一种新颖的两步路线已被开发用于寡糖的面板的合成（9 - 17）含C-2官能α-d阿拉伯呋喃糖残基。此路线的第一步是使用2,3-脱水糖硫糖苷（6）。在第二步中，用甲醇钠和叠氮化钠在C-2上将2，3-脱水糖苷中的环氧化物区域选择性地打开，从而提供具有α-d-阿拉伯呋喃糖基立体化学的产物。对这些靶标的这种方法避免了在具有在C-2处具有非参与基团的阿拉伯呋喃糖基供体的糖基化中固有的潜在的立体控制问题。该路线的收敛性也很高，可在环氧糖苷27 – 29与亲核试剂反应后制备一系列C-2'和C-2''修饰的寡糖。

  DOI：

  10.1016/j.tet.2003.12.022
• 作为产物：
  描述：

  octyl 2-O-benzoyl-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-α-D-arabinofuranoside 在 四丁基氟化铵 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 octyl 2,5-di-O-benzoyl-α-D-arabinofuranoside
  参考文献：
  名称：

  2,3-脱水糖在糖苷键合成中的作用。在制备C-2功能化的α-d-阿拉伯呋喃糖苷中的应用

  摘要：

  一种新颖的两步路线已被开发用于寡糖的面板的合成（9 - 17）含C-2官能α-d阿拉伯呋喃糖残基。此路线的第一步是使用2,3-脱水糖硫糖苷（6）。在第二步中，用甲醇钠和叠氮化钠在C-2上将2，3-脱水糖苷中的环氧化物区域选择性地打开，从而提供具有α-d-阿拉伯呋喃糖基立体化学的产物。对这些靶标的这种方法避免了在具有在C-2处具有非参与基团的阿拉伯呋喃糖基供体的糖基化中固有的潜在的立体控制问题。该路线的收敛性也很高，可在环氧糖苷27 – 29与亲核试剂反应后制备一系列C-2'和C-2''修饰的寡糖。

  DOI：

  10.1016/j.tet.2003.12.022

文献信息

• Synthesis of octyl arabinofuranosides as substrates for mycobacterial arabinosyltransferases
  作者：Jeongseok Han、Rajendrakumar Reddy Gadikota、Patrick R McCarren、Todd L Lowary

  DOI：10.1016/s0008-6215(02)00541-4

  日期：2003.3

  A panel of octyl oligosaccharides comprised of arabinofuranose rings have been synthesized via efficient and readily scaleable routes. The key glycosylation reactions involved the coupling of octyl glycoside acceptors with the appropriate thioglycosides using N-iodosuccinimide and silver triflate activation. These syntheses were undertaken to provide substrates suitable for use in assays of mycobacterial arabinosyltransferases. (C) 2003 Elsevier Science Ltd. All rights reserved.
• 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.
• Oligosaccharides as inhibitors of mycobacterial arabinosyltransferases. Di- and trisaccharides containing C-3 modified arabinofuranosyl residues
  作者：Oana M. Cociorva、Sudagar S. Gurcha、Gurdyal S. Besra、Todd L. Lowary

  DOI：10.1016/j.bmc.2004.11.003

  日期：2005.2

  The assembly of the arabinan portions of cell wall polysaccharicles in mycobacteria involves a family of arabinosyltransferases (AraT's) that promote the polymerization of decaprenolphosphoarabinose. Mycobacterial viability depends upon the ability of the organism to synthesize an intact arabinan and thus compounds that inhibit these AraT's are both useful biochemical tools as well as potential lead compounds for new anti-tuberculosis agents. We describe here the preparation of oligosaccharide fragments of mycobacterial arabinan that contain arabinofuranosyl residues modified at C-3 by the replacement of the hydroxyl group with an amino, azido or methoxy functionality. Subsequent testing of these oligosaccharides as inhibitors of mycobacterial AraT's revealed that all inhibited the enzymes, but to varying degrees. In further studies, each compound was shown to have only low activity as an inhibitor of mycobacterial growth. (C) 2004 Elsevier Ltd. All rights reserved.
• 2,3-Anhydrosugars in glycoside bond synthesis. Application to the preparation of C-2 functionalized α-d-arabinofuranosides
  作者：Oana M Cociorva、Todd L Lowary

  DOI：10.1016/j.tet.2003.12.022

  日期：2004.2

  novel two-step route has been developed for the synthesis of a panel of oligosaccharides (9–17) containing C-2 functionalized α-d-arabinofuranosyl residues. The first step in this route consists of a highly stereocontrolled glycosylation reaction using a 2,3-anhydrosugar thioglycoside (6). In the second step, the epoxide ring in the 2,3-anhydrosugar glycoside is regioselectively opened at C-2 with sodium

  一种新颖的两步路线已被开发用于寡糖的面板的合成（9 - 17）含C-2官能α-d阿拉伯呋喃糖残基。此路线的第一步是使用2,3-脱水糖硫糖苷（6）。在第二步中，用甲醇钠和叠氮化钠在C-2上将2，3-脱水糖苷中的环氧化物区域选择性地打开，从而提供具有α-d-阿拉伯呋喃糖基立体化学的产物。对这些靶标的这种方法避免了在具有在C-2处具有非参与基团的阿拉伯呋喃糖基供体的糖基化中固有的潜在的立体控制问题。该路线的收敛性也很高，可在环氧糖苷27 – 29与亲核试剂反应后制备一系列C-2'和C-2''修饰的寡糖。