methyl 2,4-di-O-acetyl-3-azido-3-deoxy-5-thio-α-D-xylopyranoside | 142544-06-7

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: methyl 2,4-di-O-acetyl-3-azido-3-deoxy-5-thio-α-D-xylopyranoside
• CAS: 142544-06-7
• 化学式: C₁₀H₁₅N₃O₅S
• 分子量: 289.312
• InChiKey: GWIVWXLKICCVHW-RGOKHQFPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.25
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  110.59
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  methyl 2,4-di-O-acetyl-3-azido-3-deoxy-5-thio-α-D-xylopyranoside 在 吡啶 、 lithium aluminium tetrahydride 、 硫酸 作用下， 以 溶剂黄146 为溶剂， 反应 53.25h， 生成 3-acetamido-1,2,4-tri-O-acetyl-3-deoxy-5-thio-α-D-xylopyranoside
  参考文献：
  名称：

  3-乙酰氨基-3-脱氧-5-硫代-d-木糖和4-乙酰氨基-4-脱氧-5-硫代-l-木糖的合成和构型及其一些衍生物

  摘要：

  摘要在与叠氮化物离子反应中，将5-硫代-3-O-3-对甲苯磺酰基-α-d-吡喃吡喃糖苷甲基生成3-叠氮基-3-脱氧-5-硫代α-d-吡喃吡喃糖苷甲基4-O-。乙酰-2,3-脱水5-硫代-α-d-呋喃呋喃糖苷（7）得到甲基4-O-乙酰基-3-叠氮基-3-脱氧-5-硫代-α-d-吡喃吡喃糖苷与在乙酰化之后，将2-叠氮基-2-脱氧-d阿拉伯糖类似物和甲基2-O-乙酰基-3,4-脱水5-硫代-α-d-核吡喃糖苷（8）提供乙基2,4-二- O-乙酰基-3-脱氧-5-硫代-α-d-吡喃吡喃糖苷和甲基2，3-二-O-乙酰基-4-叠氮基-4-脱氧-5-硫代-β-l-吡喃吡喃糖苷。用甲醇氨处理7和8分别得到3-氨基-3-脱氧-5-硫代-α-d-木吡喃糖苷甲基和4-氨基-3-deixy-1 lyxo类似物，其特征为四乙酸酯14和19。

  DOI：

  10.1016/0008-6215(92)84129-g
• 作为产物：
  描述：

  methyl 5-thio-3-O-toluene-p-sulphonyl-α-D-xylopyranoside 在 吡啶 、 叠氮化锂 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 23.0h， 生成 methyl 2,4-di-O-acetyl-3-azido-3-deoxy-5-thio-α-D-xylopyranoside
  参考文献：
  名称：

  3-乙酰氨基-3-脱氧-5-硫代-d-木糖和4-乙酰氨基-4-脱氧-5-硫代-l-木糖的合成和构型及其一些衍生物

  摘要：

  摘要在与叠氮化物离子反应中，将5-硫代-3-O-3-对甲苯磺酰基-α-d-吡喃吡喃糖苷甲基生成3-叠氮基-3-脱氧-5-硫代α-d-吡喃吡喃糖苷甲基4-O-。乙酰-2,3-脱水5-硫代-α-d-呋喃呋喃糖苷（7）得到甲基4-O-乙酰基-3-叠氮基-3-脱氧-5-硫代-α-d-吡喃吡喃糖苷与在乙酰化之后，将2-叠氮基-2-脱氧-d阿拉伯糖类似物和甲基2-O-乙酰基-3,4-脱水5-硫代-α-d-核吡喃糖苷（8）提供乙基2,4-二- O-乙酰基-3-脱氧-5-硫代-α-d-吡喃吡喃糖苷和甲基2，3-二-O-乙酰基-4-叠氮基-4-脱氧-5-硫代-β-l-吡喃吡喃糖苷。用甲醇氨处理7和8分别得到3-氨基-3-脱氧-5-硫代-α-d-木吡喃糖苷甲基和4-氨基-3-deixy-1 lyxo类似物，其特征为四乙酸酯14和19。

  DOI：

  10.1016/0008-6215(92)84129-g

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.