2-deoxy-1-O-methyl-3-O-(tert-butyldiphenylsilyl)-5-O-(p-toluenesulfonyl)-D-ribofuranose | 951766-55-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-deoxy-1-O-methyl-3-O-(tert-butyldiphenylsilyl)-5-O-(p-toluenesulfonyl)-D-ribofuranose
• 英文别名: [(2R,3S)-3-[tert-butyl(diphenyl)silyl]oxy-5-methoxyoxolan-2-yl]methyl 4-methylbenzenesulfonate
• CAS: 951766-55-5
• 化学式: C₂₉H₃₆O₆SSi
• 分子量: 540.753
• InChiKey: RVUSVMPCVHMZDU-MDEZFMAYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.41
• 重原子数：
  37
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  79.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-deoxy-1-O-methyl-3-O-(tert-butyldiphenylsilyl)-5-O-(p-toluenesulfonyl)-D-ribofuranose 在 indium(III) triflate 、 间氯过氧苯甲酸 、 sodium iodide 、 锌 作用下， 以 二氯甲烷 、 二甲基亚砜 、 丙酮 为溶剂， 反应 1.5h， 生成 (3S)-3-tert-butyldiphenylsilyloxy-pent-5-enoic acid
  参考文献：
  名称：

  2-Deoxyribose as a Rich Source of Chiral 5-Carbon Building Blocks

  摘要：

  [GRAPHICS]We have developed concise routes to a number of useful chiral 5-carbon synthetic building blocks using readily available: 0-1-methyl-2-deoxyribose as starting material. Novel transformations include the use of indium triflate to catalyze the oxidation of a methyl furanoside to the corresponding lactone with MCPBA and the Vasella-type fragmentation of a 5-iodo furanoside using chromium(II) chloride when zinc proved ineffective. In addition, 3,4-disubstitued piperidine derivatives were prepared without hydroxyl group protection via a simple reductive amination reaction.

  DOI：

  10.1021/jo0712143
• 作为产物：
  描述：

  甲基-2-脱氧-D-核糖 在 吡啶 、 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-deoxy-1-O-methyl-3-O-(tert-butyldiphenylsilyl)-5-O-(p-toluenesulfonyl)-D-ribofuranose
  参考文献：
  名称：

  2-Deoxyribose as a Rich Source of Chiral 5-Carbon Building Blocks

  摘要：

  [GRAPHICS]We have developed concise routes to a number of useful chiral 5-carbon synthetic building blocks using readily available: 0-1-methyl-2-deoxyribose as starting material. Novel transformations include the use of indium triflate to catalyze the oxidation of a methyl furanoside to the corresponding lactone with MCPBA and the Vasella-type fragmentation of a 5-iodo furanoside using chromium(II) chloride when zinc proved ineffective. In addition, 3,4-disubstitued piperidine derivatives were prepared without hydroxyl group protection via a simple reductive amination reaction.

  DOI：

  10.1021/jo0712143

文献信息

• 2-Deoxyribose as a Rich Source of Chiral 5-Carbon Building Blocks
  作者：Dengjin Wang、William A. Nugent

  DOI：10.1021/jo0712143

  日期：2007.9.1

  [GRAPHICS]We have developed concise routes to a number of useful chiral 5-carbon synthetic building blocks using readily available: 0-1-methyl-2-deoxyribose as starting material. Novel transformations include the use of indium triflate to catalyze the oxidation of a methyl furanoside to the corresponding lactone with MCPBA and the Vasella-type fragmentation of a 5-iodo furanoside using chromium(II) chloride when zinc proved ineffective. In addition, 3,4-disubstitued piperidine derivatives were prepared without hydroxyl group protection via a simple reductive amination reaction.