(4S,5R,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-4-triethylsilanyloxy-1-oxa-spiro[4.4]nonan-2-one | 880550-80-1

• 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: (4S,5R,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-4-triethylsilanyloxy-1-oxa-spiro[4.4]nonan-2-one
• CAS: 880550-80-1
• 化学式: C₂₀H₄₀O₄Si₂
• 分子量: 400.706
• InChiKey: PUUHMWRTKLEGLK-ABSDTBQOSA-N

物化性质

• 熔点：
  79.2-81.0 °C
• 沸点：
  431.4±45.0 °C(Predicted)
• 密度：
  0.98±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.64
• 重原子数：
  26.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (4S,5R,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-4-triethylsilanyloxy-1-oxa-spiro[4.4]nonan-2-one 在 二异丁基氢化铝 、 甲基磺酰氯 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 甲苯 为溶剂， 反应 1.0h， 生成 (4S,5R,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-4-triethylsilanyloxy-1-oxa-spiro[4.4]non-2-ene
  参考文献：
  名称：

  Highly Stereoselective β-Anomeric Glycosidation of a 2‘-Deoxy Syn-5‘-Configured 4‘-Spironucleoside

  摘要：

  [GRAPHICS]A direct enantioselective pathway that delivers exclusively the beta-anomer of a 4'-spironucleoside has been successfully developed. The key starting material is the enantiomerically pure dihydroxy lactone 19, which has proven amenable to conversion to glycal 22 via the chloro acetonide. This intermediate is then capped as the 3,5-O-(tetraisopropyldisiloxane-1,3-diyl) glycal. The latter can enter into N-iodosuccinimide-promoted glycosidation with persilylated thymine. Only the beta anomer is formed. Ensuing deiodination and desilylation proceed quantitatively to furnish the targeted, previously elusive anomer.

  DOI：

  10.1021/jo052324h
• 作为产物：
  描述：

  三乙基氯硅烷 、 (4S,5S,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-4-hydroxy-1-oxa-spiro[4.4]nonan-2-one 在 咪唑 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以99%的产率得到(4S,5R,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-4-triethylsilanyloxy-1-oxa-spiro[4.4]nonan-2-one
  参考文献：
  名称：

  Highly Stereoselective β-Anomeric Glycosidation of a 2‘-Deoxy Syn-5‘-Configured 4‘-Spironucleoside

  摘要：

  [GRAPHICS]A direct enantioselective pathway that delivers exclusively the beta-anomer of a 4'-spironucleoside has been successfully developed. The key starting material is the enantiomerically pure dihydroxy lactone 19, which has proven amenable to conversion to glycal 22 via the chloro acetonide. This intermediate is then capped as the 3,5-O-(tetraisopropyldisiloxane-1,3-diyl) glycal. The latter can enter into N-iodosuccinimide-promoted glycosidation with persilylated thymine. Only the beta anomer is formed. Ensuing deiodination and desilylation proceed quantitatively to furnish the targeted, previously elusive anomer.

  DOI：

  10.1021/jo052324h