3-azido-3-deoxy-5-O-p-toluenesulphonyl-α-D-xylofuranose | 192517-67-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-azido-3-deoxy-5-O-p-toluenesulphonyl-α-D-xylofuranose
• 英文别名: [(3aR,5S,6S,6aR)-6-azido-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methyl 4-methylbenzenesulfonate
• CAS: 192517-67-2
• 化学式: C₁₅H₁₉N₃O₆S
• 分子量: 369.398
• InChiKey: WHBQDLAHHOQLFF-XJFOESAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.26
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  119.82
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  3-azido-3-deoxy-5-O-p-toluenesulphonyl-α-D-xylofuranose 在 吡啶 、 盐酸 、 sodium methylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 methyl 2,4-di-O-acetyl-3-azido-3-deoxy-5-thio-α-D-xylopyranoside
  参考文献：
  名称：

  Synthesis of 4-cyanophenyl 2-azido-2-deoxy- and 3-azido-3-deoxy-1,5-dithio-β-d-xylopyranosides

  摘要：

  Azidonitration of 3,4-di-O-benzoyl-1,5-anhydro-5-thio-D-threo-pent-1-enitol (3,4-di-O-benzoyl-5-thio-D-xylal) afforded a I:1 mixture of 2-azido-3,4-di-O-benzoyl-2-deoxy-1-O-nitro-5-thio-alpha-D-xylo- and lyxo-pyranosides, which were converted after separation into their 1-O-acetyl derivatives 8 and 11, respectively. Glycosidation of 8 and 11 with methanol in the presence of trimethylsilyl triflate afforded methyl 2-azido-3,4-di-O-benzoyl-2-deoxy-5-thio-alpha,beta-D-xylo- and lyxo-pyranosides in a ratio of 1:I, and 5:2, respectively. When 4-cyanothiophenol was used as acceptor for the glycosidation of 8, the anomeric thioglycosides were formed in the same ratio (1:1). Deacetylation of the beta-isomer afforded 4-cyanophenyl 2-azido-2-deoxy-1,5-dithio-beta-lxyo-pyranoside 3. 3-Azido-3-deoxy-5-S-benzoyl-1,2-O-isopropylidene-alpha-D-xylofuranose was synthesised from D-glucose in 10 steps and was converted into 1,2,4-tri-O-acetyl-3-azido-3-deoxy-5-thio-D-xylopyranose 31. Glycosidation of 31 with 4-cyanothiophenol in the presence of trimethylsilyl triflate afforded 4-cyanothiophenyl 2,4-di-O-acetyl-3-azido-3-deoxy-5-thio-alpha,beta-D-xylopyranoside in a ratio of 1:1.5. Their deacetylation gave 4-cyanophenyl 3-azido-3-deoxy-1,5-dithio-beta-D-xylopyranoside 4 and its alpha-anomer 34. Reduction of 4 with sodium borohydride-nickel chloride gave the 3-amino derivative 36, which was converted into the acetamido compound 38. Compounds 3, 3, and 36 possess high oral antithrombotic activity, which decreases on acetylation of the amino group in 38. The alpha-anomer 34 was inactive. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(97)00079-7

文献信息

• Synthesis, conformational study, glycosidase inhibitory activity and molecular docking studies of dihydroxylated 4- and 5-amino-iminosugars
  作者：Vijay M. Kasture、Navnath B. Kalamkar、Roopa J. Nair、Rakesh S. Joshi、Sushma G. Sabharwal、Dilip D. Dhavale

  DOI：10.1016/j.carres.2015.03.004

  日期：2015.5

  An efficient methodology for the synthesis of new amino iminosugars 6a, 7a and 8, starting from D-glucose, is reported. The conformational study using (1)H NMR data showed that the amino iminosugar 6a exists in the (2)C5 while; the 7a and 8 exist in the (5)C2 conformation. The inhibition activities with different glycosidases showed that 6a and 7a are poor glycosidase inhibitors. However, amino iminosugar

  报道了一种从D-葡萄糖开始合成新的氨基亚氨基糖6a，7a和8的有效方法。使用（1）H NMR数据进行的构象研究表明，氨基亚氨基糖6a存在于（2）C5中；7a和8以（5）C2构象存在。不同糖苷酶的抑制活性表明6a和7a是不良的糖苷酶抑制剂。然而，氨基亚氨基糖8显示出对β-半乳糖苷酶的选择性抑制（IC50 = 43μM，Ki = 153μM）。这些结果通过分子对接研究得到证实。