(1S,2R,6R,8R,11R)-11-chloro-10-propan-2-ylspiro[3,5,7,12-tetraoxa-10-aza-11-phosphatricyclo[6.4.0.02,6]dodecane-4,1'-cyclopentane] | 175438-82-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2R,6R,8R,11R)-11-chloro-10-propan-2-ylspiro[3,5,7,12-tetraoxa-10-aza-11-phosphatricyclo[6.4.0.02,6]dodecane-4,1'-cyclopentane]
• CAS: 175438-82-1；189949-07-3
• 化学式: C₁₃H₂₁ClNO₄P
• 分子量: 321.741
• InChiKey: VYAUBDIAGBFLEA-KZKPEIIBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S,2R,6R,8R,11R)-11-chloro-10-propan-2-ylspiro[3,5,7,12-tetraoxa-10-aza-11-phosphatricyclo[6.4.0.02,6]dodecane-4,1'-cyclopentane] 在 三乙胺 、 2-溴-4,5-二氰基咪唑 作用下， 以 氯仿 、 乙腈 为溶剂， 生成 [(3aR,5R,6S,6aR)-5-[(propan-2-ylamino)methyl]spiro[3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole-2,1'-cyclopentane]-6-yl] [(2R,3S,5R)-3-[tert-butyl(dimethyl)silyl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl [(2R,3S,5R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] phosphite
  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：

  1,2-O-cyclopentylidene-5-tosyl-α-D-xylofuranose 在 三乙胺 、 三氯化磷 作用下， 以 氯仿 为溶剂， 生成 (1S,2R,6R,8R,11R)-11-chloro-10-propan-2-ylspiro[3,5,7,12-tetraoxa-10-aza-11-phosphatricyclo[6.4.0.02,6]dodecane-4,1'-cyclopentane]
  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.