Toluene-4-sulfonic acid (2R,4aR,6S,7R,8S,8aR)-8-benzyloxy-2-phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester | 863297-02-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Toluene-4-sulfonic acid (2R,4aR,6S,7R,8S,8aR)-8-benzyloxy-2-phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester
• CAS: 863297-02-3
• 化学式: C₃₃H₃₂O₇S₂
• 分子量: 604.745
• InChiKey: JSBJJJMLBBYEFS-NMVLBWOISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.29
• 重原子数：
  42.0
• 可旋转键数：
  9.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  80.29
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  Toluene-4-sulfonic acid (2R,4aR,6S,7R,8S,8aR)-8-benzyloxy-2-phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester 在 palladium on activated charcoal 吡啶 、 叠氮基三甲基硅烷 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 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 、 对甲苯磺酰氯 在 sodium hydroxide 、 potassium carbonate 作用下， 反应 4.0h， 以87%的产率得到Toluene-4-sulfonic acid (2R,4aR,6S,7R,8S,8aR)-8-benzyloxy-2-phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester
  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