methyl 3-azido-3-deoxy-α-D-arabinofuranoside | 66108-04-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-azido-3-deoxy-α-D-arabinofuranoside
• 英文别名: (2S,3S,4S,5S)-4-azido-5-(hydroxymethyl)-2-methoxyoxolan-3-ol
• CAS: 66108-04-1
• 化学式: C₆H₁₁N₃O₄
• 分子量: 189.171
• InChiKey: PLIZWGBKRRYANG-ZXXMMSQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  73.3
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 3-azido-3-deoxy-α-D-arabinofuranoside 在 吡啶 、 lithium aluminium tetrahydride 、 叔丁基二甲硅基三氟甲磺酸酯 作用下， 以 乙醚 、 乙腈 为溶剂， 反应 46.0h， 生成 1-(5-O-para-monomethoxytrityl-2,3-dideoxy-epimino-β-D-ribofuranosyl)thymine
  参考文献：
  名称：

  Synthesis of Some New Nucleoside Analogues as Potential Antiviral Agents

  摘要：

  A novel series of pyrimidine nucleoside analogues was synthesized. 2,3-Dideoxy-2,3-anhydro-beta-D-lyxofuranose was opened by sodium azide to give the corresponding azido compound, which was reduced by lithium aluminium hydride to lead to 2,3-dideoxy-2,3-epimino-beta-D-ribofuranose. Pyrimidine bases were glycosylated with this synthon to give potential antiviral molecules : 1-(2,3-dideoxy-2,3-epimino-beta-D-ribofuranosyl)pyrimidines.

  DOI：

  10.1080/07328319308018562
• 作为产物：
  描述：

  methyl 2,3-anhydro-α-D-lyxofuranoside 在 sodium azide 、 氯化铵 作用下， 以 乙醇 、 水 为溶剂， 反应 24.0h， 生成 methyl 3-azido-3-deoxy-α-D-arabinofuranoside
  参考文献：
  名称：

  Oligosaccharides as inhibitors of mycobacterial arabinosyltransferases. Di- and trisaccharides containing C-3 modified arabinofuranosyl residues

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2004.11.003

文献信息

• Convenient preparation of 3,5-anhydro- and 2,5-anhydropentofuranosides, and 5,6-anhydro-d-glucofuranose by use of the Mitsunobu reaction
  作者：Oliver Schulze、Jürgen Voss、Gunadi Adiwidjaja

  DOI：10.1016/j.carres.2004.12.027

  日期：2005.3

  osides are obtained by use of the Mitsunobu reaction from 2-O-protected methyl alpha-D-xylofuranosides, which are easily prepared from D-xylose. The Mitsunobu reaction of methyl 3-N-benzylamino-3-deoxy- and 3-azido-3-deoxyarabinofuranosides, which are prepared from the conveniently available methyl 2,3-anhydro-alpha-D- and 2,3-anhydro-alpha-l-lyxofuranosides by nucleophilic ring opening, yields the

  通过使用Mitsunobu反应，由2-O-保护的甲基α-D-木呋喃糖苷获得甲基3，5-脱水α-D-木呋喃糖苷，其可以容易地由D-木糖制备。3-N-苄氨基-3-脱氧呋喃糖和3-叠氮基3-脱氧阿拉伯呋喃糖苷的光延反应，由可方便获得的甲基2,3-脱水α-D-和2,3-脱水α-制备通过亲核开环生成-1-呋喃呋喃糖苷，得到相应的甲基2，5-脱水α-D-和2，5-脱水α-1-呋喃糖苷。3，5-脱水-1，2-O-异亚丙基-α-D-木呋喃糖与叠氮化物的开环产生相应的5-叠氮基衍生物。产物的结构和构型通过NMR光谱确认。5,6-脱水-1,2-O-异亚丙基-α-D-葡糖呋喃糖是通过1的Mitsunobu反应形成的 2-O-异亚丙基-α-D-葡萄糖呋喃糖。通过单晶X射线衍射分析验证了其结构。
• Biosynthetic Glycan Labeling
  作者：Victoria M. Marando、Daria E. Kim、Phillip J. Calabretta、Matthew B. Kraft、Bryan D. Bryson、Laura L. Kiessling

  DOI：10.1021/jacs.1c07430

  日期：2021.10.13

  Glycans are ubiquitous and play important biological roles, yet chemical methods for probing their structure and function within cells remain limited. Strategies for studying other biomacromolecules, such as proteins, often exploit chemoselective reactions for covalent modification, capture, or imaging. Unlike amino acids that constitute proteins, glycan building blocks lack distinguishing reactivity

  聚糖无处不在，发挥着重要的生物学作用，但探测其在细胞内结构和功能的化学方法仍然有限。研究其他生物大分子（例如蛋白质）的策略通常利用化学选择性反应进行共价修饰、捕获或成像。与构成蛋白质的氨基酸不同，聚糖结构单元缺乏独特的反应性，因为它们主要由多元醇异构体组成。此外，通过基因操作编码聚糖变体是复杂的。因此，我们制定了一种新的、可推广的化学选择性聚糖修饰策略，直接利用细胞糖基转移酶。许多这些酶对它们产生的产物具有选择性，但它们的供体偏好却是混杂的。因此，我们设计了具有生物正交手柄的试剂，作为糖基转移酶底物替代物。我们通过合成和测试d-阿拉伯呋喃糖 ( d -Ara f ) 探针验证了这种方法的可行性，d-阿拉伯呋喃糖是细菌中发现的一种单糖，也是保护分枝杆菌（包括结核分枝杆菌）细胞壁的重要组成部分。结果是第一个能够选择性标记含有阿拉伯呋喃糖的聚糖的探针。我们的研究作为开发其他特殊单糖的新化学选择性
• Synthesis of Some New Nucleoside Analogues as Potential Antiviral Agents
  作者：M. A. Forestier、A. I. Ayi、R. Condom、B. P. Boyode、J. N. Colin、J. Selway、R. Challand、R. Guedj

  DOI：10.1080/07328319308018562

  日期：1993.11

  A novel series of pyrimidine nucleoside analogues was synthesized. 2,3-Dideoxy-2,3-anhydro-beta-D-lyxofuranose was opened by sodium azide to give the corresponding azido compound, which was reduced by lithium aluminium hydride to lead to 2,3-dideoxy-2,3-epimino-beta-D-ribofuranose. Pyrimidine bases were glycosylated with this synthon to give potential antiviral molecules : 1-(2,3-dideoxy-2,3-epimino-beta-D-ribofuranosyl)pyrimidines.
• 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.