[(1R,2R,3S,4S,5R,7S)-3,4-diacetyloxy-7-(hydroxymethyl)-6,8-dioxabicyclo[3.2.1]octan-2-yl] acetate | 665054-22-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(1R,2R,3S,4S,5R,7S)-3,4-diacetyloxy-7-(hydroxymethyl)-6,8-dioxabicyclo[3.2.1]octan-2-yl] acetate
• CAS: 665054-22-8
• 化学式: C₁₃H₁₈O₉
• 分子量: 318.281
• InChiKey: GLWAABQHOYUDNM-JQPUBBMISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 [(1R,2R,3S,4S,5R,7S)-3,4-diacetyloxy-7-(hydroxymethyl)-6,8-dioxabicyclo[3.2.1]octan-2-yl] acetate 在 硫酸 作用下， 以 吡啶 为溶剂， 以91%的产率得到L-glycero-D-manno-heptopyranose hexa-acetate
  参考文献：
  名称：

  A novel stereoselective carbon-chain extension reaction at the C-6 position of 1,6-anhydropyranose

  摘要：

  6-Bromo-1,6-anhydro-D-mannose triacetate reacted with a variety of carbon nucleophiles such as allylsilane, silylacetylenes, propargylsilane, and aromatic compounds in the presence of silver triflate to give the corresponding chain extended products at C-6 in high exo-selectivities. The product obtained from the reaction with propargylsilane was efficiently transformed into a naturally occurring heptopyranose derivative found in bacteria] lipopolysaccharide. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.10.135
• 作为产物：
  描述：

  6-bromo-1,6-anhydro-D-mannose triacetate 在 silver trifluoromethanesulfonate 、 臭氧 作用下， 以 二氯甲烷 为溶剂， 生成 [(1R,2R,3S,4S,5R,7S)-3,4-diacetyloxy-7-(hydroxymethyl)-6,8-dioxabicyclo[3.2.1]octan-2-yl] acetate
  参考文献：
  名称：

  A novel stereoselective carbon-chain extension reaction at the C-6 position of 1,6-anhydropyranose

  摘要：

  6-Bromo-1,6-anhydro-D-mannose triacetate reacted with a variety of carbon nucleophiles such as allylsilane, silylacetylenes, propargylsilane, and aromatic compounds in the presence of silver triflate to give the corresponding chain extended products at C-6 in high exo-selectivities. The product obtained from the reaction with propargylsilane was efficiently transformed into a naturally occurring heptopyranose derivative found in bacteria] lipopolysaccharide. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.10.135