4,6-O-di-tert-butylsilylidene-2-deoxy-D-lyxo-1,5-hexonolactone | 1157997-31-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 4,6-O-di-tert-butylsilylidene-2-deoxy-D-lyxo-1,5-hexonolactone
• CAS: 1157997-31-3
• 化学式: C₁₄H₂₆O₅Si
• 分子量: 302.443
• InChiKey: LWQRGYZDXJTUDT-CKYFFXLPSA-N

物化性质

• 沸点：
  431.3±45.0 °C(predicted)
• 密度：
  1.10±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.12
• 重原子数：
  20.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  64.99
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4,6-O-di-tert-butylsilylidene-2-deoxy-D-lyxo-1,5-hexonolactone 在 2-碘酰基苯甲酸 、 phthalimidesulfenyl chloride 作用下， 以 乙酸乙酯 、 氯仿 为溶剂， 反应 3.75h， 生成 (4aR,8aS)-2,2-di-tert-butyl-7-thioxodihydropyrano[3,2-d][1,3,2]dioxasiline-6,8(4H,7H)-dione
  参考文献：
  名称：

  Stereoselective Synthesis of 1,3-Disaccharides through Diels-Alder Reactions: Part 2^{[ ]}: Convenient Protecting Groups for Heterodienes and Conformational Evaluations

  摘要：

  Improved synthesis of 1,3-disaccharides, obtained diastereomerically pure by [4+2] hetero cycloadditions between glycals and -thiono- -keto- -lactones, has been reported. The choice of appropriate protecting groups for -keto- -lactones, stable under cycloaddition conditions employed, sensibly shortened the synthesis of heterodienic precursors. The first example of a -oxy-imino- -lactone synthesized from -keto- -lactones was also reported. Molecular modeling and conformational evaluations about the cycloaddition features allowed tentatively rationalizing the experimental results.

  DOI：

  10.1080/07328300902752223
• 作为产物：
  描述：

  4,6-O-di-tert-butylsililydene-2-deoxy-D-galactopyranose 在 silver carbonate 作用下， 以 苯 为溶剂， 反应 3.0h， 以88%的产率得到4,6-O-di-tert-butylsilylidene-2-deoxy-D-lyxo-1,5-hexonolactone
  参考文献：
  名称：

  Stereoselective Synthesis of 1,3-Disaccharides through Diels-Alder Reactions: Part 2^{[ ]}: Convenient Protecting Groups for Heterodienes and Conformational Evaluations

  摘要：

  Improved synthesis of 1,3-disaccharides, obtained diastereomerically pure by [4+2] hetero cycloadditions between glycals and -thiono- -keto- -lactones, has been reported. The choice of appropriate protecting groups for -keto- -lactones, stable under cycloaddition conditions employed, sensibly shortened the synthesis of heterodienic precursors. The first example of a -oxy-imino- -lactone synthesized from -keto- -lactones was also reported. Molecular modeling and conformational evaluations about the cycloaddition features allowed tentatively rationalizing the experimental results.

  DOI：

  10.1080/07328300902752223