(2R,3R,4R,5S,6R)-3-Azido-5-benzyloxy-6-hydroxymethyl-2-phenylsulfanyl-tetrahydro-pyran-4-ol | 173465-76-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4R,5S,6R)-3-Azido-5-benzyloxy-6-hydroxymethyl-2-phenylsulfanyl-tetrahydro-pyran-4-ol
• CAS: 173465-76-4
• 化学式: C₁₉H₂₁N₃O₄S
• 分子量: 387.459
• InChiKey: PQCLZIGAZNEAHP-FVVUREQNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.12
• 重原子数：
  27.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  107.68
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  二叔丁基硅基双(三氟甲烷磺酸) 、 (2R,3R,4R,5S,6R)-3-Azido-5-benzyloxy-6-hydroxymethyl-2-phenylsulfanyl-tetrahydro-pyran-4-ol 在 2,6-二甲基吡啶 作用下， 反应 2.0h， 以0.631 g的产率得到phenyl 2-azido-4-O-benzyl-(di-tert-butylsilylene)-2-deoxy-1-thio-α-D-glucopyranoside
  参考文献：
  名称：

  Conformationally Armed 3,6-Tethered Glycosyl Donors: Synthesis, Conformation, Reactivity, and Selectivity

  摘要：

  The reactivity and selectivity of 3,6-tethered glycosyl donors have been studied using acceptors with different steric and electronic characteristics. Eight (four anomeric pairs) 3,6-bridged-glycosyl donors were synthesized in high yields from their common parent sugars. The glycosylation properties were tested using at least three different acceptors and several promoter systems. Thiophenyl 2,4-di-O-benzyl-3,6-O-(di-tert-butylsilylene)-alpha-D-glucopyranoside gave alpha/beta mixtures with standard NIS/TfOH mediated activation, whereas the corresponding fluoride was found to be highly beta-selective, when using SnCl2/AgE(C6F5)(4) as the promoter system. Mannosyl donors were highly alpha-selective despite the altered conformation. Galactosylations using NIS/TfOH were generally alpha-selective, but more beta-selective using the galactosyl fluoride and depending on the acceptor used. Thiophenyl 2-azido-2-deoxy-4-O-benzyl-3,6-O-(di-tert-butylsilylene)-alpha-D-glucopyranoside was found to be alpha-selective. The reactivity of the donors was investigated using competition experiments, and some but not all were found to be highly reactive. Generally it was found that the alpha-thioglycosides were significantly more reactive than the beta; this difference in reactivity was not found for 3,6-anhydro-, armed-(benzylated), or the classic super armed (silylated) donors. A mechanism supporting the unusual observations has been suggested.

  DOI：

  10.1021/jo4012464
• 作为产物：
  描述：

  3-O-acetyl-2-azido-4-O-benzyl-1,6-anhydroglucose 在 sodium methylate 、 zinc(II) iodide 作用下， 以 1,2-二氯乙烷 为溶剂， 生成 (2R,3R,4R,5S,6R)-3-Azido-5-benzyloxy-6-hydroxymethyl-2-phenylsulfanyl-tetrahydro-pyran-4-ol
  参考文献：
  名称：

  生物活性脂质类似物14 C标记的合成途径

  摘要：

  通过冷实验建立了14 C-标记大肠杆菌脂质A的膦酰氧乙基（PE）类似物的合成途径。PE类似物在化学上比天然脂质A更稳定，但显示出实际上相同的生物学活性。通过使用高价碘试剂PhIO-SnClO 4 -AgClO 4作为活化剂，用α-二糖硫代糖苷实现乙二醇单元作为14 C标记位置的糖基化。在CH 3 CNCH 2 Cl 2中，通过三氟甲磺酸三甲基甲硅烷基酯选择性地除去了用于保护乙二醇的远端羟基的对甲氧基苄基。 然后磷酸化和脱保护得到目标化合物。

  DOI：

  10.1016/0040-4039(95)01863-d