4-cyanophenyl 3-amino-3-deoxy-1,5-dithio-β-D-xylopyranoside | 192517-77-4

• 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: 4-cyanophenyl 3-amino-3-deoxy-1,5-dithio-β-D-xylopyranoside
• 英文别名: 4-[(2S,3R,4S,5S)-4-amino-3,5-dihydroxythian-2-yl]sulfanylbenzonitrile
• CAS: 192517-77-4
• 化学式: C₁₂H₁₄N₂O₂S₂
• 分子量: 282.387
• InChiKey: ITTRITOHUBGQEI-KXNHARMFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  141
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-cyanophenyl 3-amino-3-deoxy-1,5-dithio-β-D-xylopyranoside 在 吡啶 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 N-[(2S,3R,4S,5S)-2-(4-cyanophenyl)sulfanyl-3,5-dihydroxythian-4-yl]acetamide
  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
• 作为产物：
  描述：

  4-巯基苯甲腈 在 sodium tetrahydroborate 、 三氟甲磺酸三甲基硅酯 、 sodium methylate 、 nickel dichloride 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 8.5h， 生成 4-cyanophenyl 3-amino-3-deoxy-1,5-dithio-β-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 of 4-cyanophenyl 2-azido-2-deoxy- and 3-azido-3-deoxy-1,5-dithio-β-d-xylopyranosides
  作者：Éva Bozó、Sándor Boros、János Kuszmann

  DOI：10.1016/s0008-6215(97)00079-7

  日期：1997.6

  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.