1-[(2R,4S,5R)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-[[(1S,2R,6R,8R,11S)-4,4-dimethyl-10-propan-2-yl-3,5,7,12-tetraoxa-10-aza-11-phosphatricyclo[6.4.0.02,6]dodecan-11-yl]oxy]oxolan-2-yl]-5-methylpyrimidine-2,4-dione | 207598-54-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: 1-[(2R,4S,5R)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-[[(1S,2R,6R,8R,11S)-4,4-dimethyl-10-propan-2-yl-3,5,7,12-tetraoxa-10-aza-11-phosphatricyclo[6.4.0.02,6]dodecan-11-yl]oxy]oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 207598-54-7
• 化学式: C₂₇H₄₆N₃O₉PSi
• 分子量: 615.736
• InChiKey: PIWAWKSFCUNANW-DBMKMUPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.75
• 重原子数：
  41
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  117
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1-[(2R,4S,5R)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-[[(1S,2R,6R,8R,11S)-4,4-dimethyl-10-propan-2-yl-3,5,7,12-tetraoxa-10-aza-11-phosphatricyclo[6.4.0.02,6]dodecan-11-yl]oxy]oxolan-2-yl]-5-methylpyrimidine-2,4-dione 在 苯基二硫化物 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 生成 1-[(2R,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-((2R,4aR,5aR,8aR,8bS)-3-isopropyl-7,7-dimethyl-2-thioxo-hexahydro-2λ⁵-[1,3]dioxolo[4,5]furo[2,3-e][1,3,2]oxazaphosphinin-2-yloxy)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione
  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 1-[(2R,4S,5R)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-[[(1S,2R,6R,8R,11S)-4,4-dimethyl-10-propan-2-yl-3,5,7,12-tetraoxa-10-aza-11-phosphatricyclo[6.4.0.02,6]dodecan-11-yl]oxy]oxolan-2-yl]-5-methylpyrimidine-2,4-dione
  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.