(2S,4aR,5aR,8aR,8bS)-2-Isopropoxy-3-isopropyl-7,7-dimethyl-hexahydro-[1,3]dioxolo[4,5]furo[2,3-e][1,3,2]oxazaphosphinine | 207598-55-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,4aR,5aR,8aR,8bS)-2-Isopropoxy-3-isopropyl-7,7-dimethyl-hexahydro-[1,3]dioxolo[4,5]furo[2,3-e][1,3,2]oxazaphosphinine
• 英文别名: (1S,2R,6R,8R,11S)-4,4-dimethyl-10-propan-2-yl-11-propan-2-yloxy-3,5,7,12-tetraoxa-10-aza-11-phosphatricyclo[6.4.0.02,6]dodecane
• CAS: 207598-55-8
• 化学式: C₁₄H₂₆NO₅P
• 分子量: 319.338
• InChiKey: PYGSDZSCRCPCTR-BHZJTRKSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  49.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,4aR,5aR,8aR,8bS)-2-Isopropoxy-3-isopropyl-7,7-dimethyl-hexahydro-[1,3]dioxolo[4,5]furo[2,3-e][1,3,2]oxazaphosphinine 在 苯基二硫化物 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 生成 (2R,4aR,5aR,8aR,8bS)-2-Isopropoxy-3-isopropyl-7,7-dimethyl-hexahydro-[1,3]dioxolo[4,5]furo[2,3-e][1,3,2]oxazaphosphinine 2-sulfide
  参考文献：
  名称：

  Stereoselective Synthesis of Dithymidine Phosphorothioates Using Xylose Derivatives as Chiral Auxiliaries

  摘要：

  1,2-O-Cyclopentylidene-5-deoxy-5-isopropylamino-alpha-D-xylofuranose 1 and its enantiomer 11 were used as chiral auxiliaries to form, respectively, Sp and Rp dithymidine phosphorothioates 9 and 10 in 98% diastereomeric excess, using phosphoramidite methodology and 2-bromo-4,5-dicyanoimidazole as catalyst. The stereochemistry of the coupling reaction is discussed.

  DOI：

  10.1021/jo972318o
• 作为产物：
  描述：

  5-deoxy-5-isopropylamino-1,2-O-isopropylidene-α-D-xylofuranose 在 三乙胺 、 三氯化磷 作用下， 以 氯仿 为溶剂， 生成 (2S,4aR,5aR,8aR,8bS)-2-Isopropoxy-3-isopropyl-7,7-dimethyl-hexahydro-[1,3]dioxolo[4,5]furo[2,3-e][1,3,2]oxazaphosphinine
  参考文献：
  名称：

  Stereoselective Synthesis of Dithymidine Phosphorothioates Using Xylose Derivatives as Chiral Auxiliaries

  摘要：

  1,2-O-Cyclopentylidene-5-deoxy-5-isopropylamino-alpha-D-xylofuranose 1 and its enantiomer 11 were used as chiral auxiliaries to form, respectively, Sp and Rp dithymidine phosphorothioates 9 and 10 in 98% diastereomeric excess, using phosphoramidite methodology and 2-bromo-4,5-dicyanoimidazole as catalyst. The stereochemistry of the coupling reaction is discussed.

  DOI：

  10.1021/jo972318o

文献信息

• Stereoselective Synthesis of Dithymidine Phosphorothioates Using Xylose Derivatives as Chiral Auxiliaries
  作者：Yi Jin、George Just

  DOI：10.1021/jo972318o

  日期：1998.5.1

  1,2-O-Cyclopentylidene-5-deoxy-5-isopropylamino-alpha-D-xylofuranose 1 and its enantiomer 11 were used as chiral auxiliaries to form, respectively, Sp and Rp dithymidine phosphorothioates 9 and 10 in 98% diastereomeric excess, using phosphoramidite methodology and 2-bromo-4,5-dicyanoimidazole as catalyst. The stereochemistry of the coupling reaction is discussed.