Methanesulfonic acid (2R,4aR,6R,7S,8S,8aR)-8-benzyloxy-2-phenyl-6-tritylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester | 863297-16-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: Methanesulfonic acid (2R,4aR,6R,7S,8S,8aR)-8-benzyloxy-2-phenyl-6-tritylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester
• 英文别名: [(2R,4aR,6R,7S,8S,8aR)-2-phenyl-8-phenylmethoxy-6-tritylsulfanyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl] methanesulfonate
• CAS: 863297-16-9
• 化学式: C₄₀H₃₈O₇S₂
• 分子量: 694.87
• InChiKey: CONWZOOGCFDSIA-HAWFYAJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  49
• 可旋转键数：
  11
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Methanesulfonic acid (2R,4aR,6R,7S,8S,8aR)-8-benzyloxy-2-phenyl-6-tritylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester 在 sodium azide 作用下， 以 乙腈 、 丁酮 为溶剂， 生成 (2R,4aR,8S,8aR)-8-Benzyloxy-2-phenyl-7-tritylsulfanyl-4,4a,8,8a-tetrahydro-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
• 作为产物：
  描述：

  triphenylmethyl 1-thio-α-D-mannopyranoside 在 吡啶 、 二正丁基氧化锡 、 对甲苯磺酸 、 cesium fluoride 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 13.0h， 生成 Methanesulfonic acid (2R,4aR,6R,7S,8S,8aR)-8-benzyloxy-2-phenyl-6-tritylsulfanyl-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

文献信息

• Glycosyl azides of sugar 2-sulfonic acids
  作者：Ferenc Sajtos、László Lázár、Anikó Borbás、István Bajza、András Lipták

  DOI：10.1016/j.tetlet.2005.05.112

  日期：2005.8

  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.