1-O-acetyl-2-azido-2-deoxy-3,4-di-O-benzoyl-5-thio-α-D-lyxopyranose | 192517-51-4

• 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: 1-O-acetyl-2-azido-2-deoxy-3,4-di-O-benzoyl-5-thio-α-D-lyxopyranose
• CAS: 192517-51-4
• 化学式: C₂₁H₁₉N₃O₆S
• 分子量: 441.464
• InChiKey: CBTRZEHTGVJVIA-WKRCXCSHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.75
• 重原子数：
  31.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  127.66
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  1-O-acetyl-2-azido-2-deoxy-3,4-di-O-benzoyl-5-thio-α-D-lyxopyranose 在 三氟化硼乙醚 、 sodium methylate 作用下， 以 甲醇 、 1,2-二氯乙烷 为溶剂， 反应 25.0h， 生成 4-nitrophenyl 2-azido-2-deoxy-1,5-dithio-β-D-lyxopyranoside
  参考文献：
  名称：

  具有抗血栓形成活性的4-氰基苯基和4-硝基苯基2-叠氮基-2-脱氧-1,5-二硫-β-D-阿拉伯糖基-和-β-D-吡喃吡喃糖苷的合成。

  摘要：

  将三-O-乙酰基-5-硫代-D-核吡喃糖基溴化物转化为3,4-二-O-苯甲酰基-1,5-脱水5-硫代-D-赤型戊-1-烯醇（3,4 -二-O-苯甲酰基-5-硫代-D-ribal），将其叠氮基化得到2-叠氮基-3,4-二-O-苯甲酰基-2-脱氧-1-O-硝基-5的不稳定混合物-硫代-D-戊吡喃糖苷++ +异构体。将其不分离地转化成相应的1-O-乙酰基衍生物，1-O-乙酰基-2-叠氮基3，4-二-O-苯甲酰基-2-脱氧-5-基的α，β异头混合物。可以高产率分离出硫代-D-阿拉伯糖吡喃糖+++异构体。分别使用三甲基硅烷基三氟甲磺酸酯或三氟化硼醚化物作为促进剂，用4-氰基或4-硝基苯硫醇对该混合物进行糖基化，仅得到相应的D异头物。Zemplén脱苯甲酰化得到4-氰基苯基以及4-硝基苯基2-叠氮基-2-脱氧-1 5-二硫代-β-D-阿拉伯吡喃糖苷分别。当使用1-O-乙酰基-2-叠氮基-3,4-二-O

  DOI：

  10.1016/s0008-6215(99)00320-1
• 作为产物：
  描述：

  sodium acetate 、 2-azido-2-deoxy-3,4-di-O-benzoyl-1-O-nitro-5-thio-α-D-lyxopyranose 以 溶剂黄146 为溶剂， 反应 1.0h， 以29%的产率得到1-O-acetyl-2-azido-2-deoxy-3,4-di-O-benzoyl-5-thio-α-D-lyxopyranose
  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