(S)-2-hydroxy-2-((4R,4'R,5R)-2,2,2',2'-tetramethyl-[4,4'-bi(1,3-dioxolan)]-5-yl)ethyl methanesulfonate | 947669-08-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-2-hydroxy-2-((4R,4'R,5R)-2,2,2',2'-tetramethyl-[4,4'-bi(1,3-dioxolan)]-5-yl)ethyl methanesulfonate
• CAS: 947669-08-1
• 化学式: C₁₃H₂₄O₈S
• 分子量: 340.395
• InChiKey: PTZCWEODHXZWLL-LNFKQOIKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.0
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  100.52
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (S)-2-hydroxy-2-((4R,4'R,5R)-2,2,2',2'-tetramethyl-[4,4'-bi(1,3-dioxolan)]-5-yl)ethyl methanesulfonate 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 (1S)-2-azido-1-[(4R,5R)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]ethanol
  参考文献：
  名称：

  New Access to 1-Deoxynojirimycin Derivatives via Azide−Alkene Cycloaddition

  摘要：

  The synthesis of 1-deoxynojirimycin (DNJ) derivatives is described from D-glucono-delta-lactone. The DNJ derivatives were obtained via a sequence that included a stereoselective intramolecular Huisgen reaction, decomposition to an aziridine, and its subsequent reaction with a nucleophile. Minimization of allylic strain in the transition state accounts for the stereoselectivity of the cycloaddition reaction.

  DOI：

  10.1021/ol8014495
• 作为产物：
  描述：

  甲基磺酰氯 、 (S)-1-((4R,4'R,5R)-2,2,2',2'-tetramethyl-4,4'-bi(1,3-dioxolan)-5-yl)ethane-1,2-diol 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 以11.7 g的产率得到(S)-2-hydroxy-2-((4R,4'R,5R)-2,2,2',2'-tetramethyl-[4,4'-bi(1,3-dioxolan)]-5-yl)ethyl methanesulfonate
  参考文献：
  名称：

  New Access to 1-Deoxynojirimycin Derivatives via Azide−Alkene Cycloaddition

  摘要：

  The synthesis of 1-deoxynojirimycin (DNJ) derivatives is described from D-glucono-delta-lactone. The DNJ derivatives were obtained via a sequence that included a stereoselective intramolecular Huisgen reaction, decomposition to an aziridine, and its subsequent reaction with a nucleophile. Minimization of allylic strain in the transition state accounts for the stereoselectivity of the cycloaddition reaction.

  DOI：

  10.1021/ol8014495