(2R,4aR,6R,7S,8S,8aR)-6-Azido-8-benzyloxy-2-phenyl-7-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxine | 863297-06-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: (2R,4aR,6R,7S,8S,8aR)-6-Azido-8-benzyloxy-2-phenyl-7-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxine
• CAS: 863297-06-7
• 化学式: C₂₆H₂₅N₃O₄S
• 分子量: 475.568
• InChiKey: ULOCGJZOHDKDLI-PSRUHSIGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.88
• 重原子数：
  34.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  85.68
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (2R,4aR,6R,7S,8S,8aR)-6-Azido-8-benzyloxy-2-phenyl-7-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxine 在 三苯基膦 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成
  参考文献：
  名称：

  Glycosyl azides of sugar 2-sulfonic acids

  摘要：

  Phenyl and trityl 2-O-stilfonyl-1-thio-alpha-D-manno- and beta-D-glucopyranosides were reacted with sodium azide to yield 2-S-phenyl or 2-S-trityl-D-gluco- and D-mannopyranosyl azides, respectively. Usually, both anomers were formed in approximately equal amounts and formation of glycals was also observed in some cases. The product distribution of these reactions depends on the nature of the aglycone, the applied reagent and also on the solvent. These results can be rationalised by the intermediacy of episulfonium as well as oxocarbenium ions. Oxidation of the 2-S-trityl-alpha-D-glycopyranosyl or alpha-D-mannopyranosyl azides by Oxone (R). gave sodium 2-sulfonato-alpha-D-gluco- and alpha-D-mannopyranosyl azides, respectively. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.05.112
• 作为产物：
  描述：

  phenyl 3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside 在 sodium hydroxide 、 sodium azide 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 (2R,4aR,6R,7S,8S,8aR)-6-Azido-8-benzyloxy-2-phenyl-7-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxine
  参考文献：
  名称：

  Glycosyl azides of sugar 2-sulfonic acids

  摘要：

  Phenyl and trityl 2-O-stilfonyl-1-thio-alpha-D-manno- and beta-D-glucopyranosides were reacted with sodium azide to yield 2-S-phenyl or 2-S-trityl-D-gluco- and D-mannopyranosyl azides, respectively. Usually, both anomers were formed in approximately equal amounts and formation of glycals was also observed in some cases. The product distribution of these reactions depends on the nature of the aglycone, the applied reagent and also on the solvent. These results can be rationalised by the intermediacy of episulfonium as well as oxocarbenium ions. Oxidation of the 2-S-trityl-alpha-D-glycopyranosyl or alpha-D-mannopyranosyl azides by Oxone (R). gave sodium 2-sulfonato-alpha-D-gluco- and alpha-D-mannopyranosyl azides, respectively. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.05.112