2-deoxy-1,4-O2,3-anhydro-2-<3,4-dihydro-4-oxo-5-methyl-1(2H)-pyrimidinyl>-5-O-(tert-butyldimethylsilyl)-D-lyxitol | 149097-65-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2-deoxy-1,4-O2,3-anhydro-2-<3,4-dihydro-4-oxo-5-methyl-1(2H)-pyrimidinyl>-5-O-(tert-butyldimethylsilyl)-D-lyxitol
• 英文别名: 2-deoxy-1,4-O²,3-anhydro-2-<3,4-dihydro-4-oxo-5-methyl-1(2H)-pyrimidinyl>-5-O-(tert-butyldimethylsilyl)-D-lyxitol
• CAS: 149097-65-4
• 化学式: C₁₆H₂₆N₂O₄Si
• 分子量: 338.479
• InChiKey: KKGVAJPKZDKEGN-JHJVBQTASA-N

物化性质

• 沸点：
  384.2±52.0 °C(predicted)
• 密度：
  1.22±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.27
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  62.58
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-deoxy-1,4-O2,3-anhydro-2-<3,4-dihydro-4-oxo-5-methyl-1(2H)-pyrimidinyl>-5-O-(tert-butyldimethylsilyl)-D-lyxitol 在 吡啶 、 sodium hydroxide 、 叠氮化锂 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.5h， 生成
  参考文献：
  名称：

  Synthesis of Isonucleosides Related to AZT and AZU

  摘要：

  Approaches to 1,4-anhydro-3-azido-2,3-dideoxy-2-[3,4-dihydro-2,4-dioxo-5-methyl-1(2H)-pyrimidinyl]-D-arabinitol, and the related uracil derivative, have been developed. These conceptually new, optically active analogs of AZT, derived from 1,4-anhydro-D-ribitol, are among the first examples of regioisomeric analogs of AZT.

  DOI：

  10.1080/15257779408013230
• 作为产物：
  描述：

  1,4-anhydro-2-azido-2-deoxy-3,5-O-(1,1,3,3-tetraisopropyl-1,3-disiloxanediyl)-D-arabinitol 在 palladium on activated charcoal 吡啶 、 4-二甲氨基吡啶 、 硫酸 、 氢气 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 25.0 ℃ 、275.79 kPa 条件下， 反应 59.0h， 生成 2-deoxy-1,4-O2,3-anhydro-2-<3,4-dihydro-4-oxo-5-methyl-1(2H)-pyrimidinyl>-5-O-(tert-butyldimethylsilyl)-D-lyxitol
  参考文献：
  名称：

  Synthesis of Isonucleosides Related to AZT and AZU

  摘要：

  Approaches to 1,4-anhydro-3-azido-2,3-dideoxy-2-[3,4-dihydro-2,4-dioxo-5-methyl-1(2H)-pyrimidinyl]-D-arabinitol, and the related uracil derivative, have been developed. These conceptually new, optically active analogs of AZT, derived from 1,4-anhydro-D-ribitol, are among the first examples of regioisomeric analogs of AZT.

  DOI：

  10.1080/15257779408013230

文献信息

• Synthetic Approaches to New Regioisomers of AZT and AZU
  作者：Vasu Nair、David F. Purdy

  DOI：10.3987/com-92-6175

  日期：——

  Approaches to 1,4-anhydro-3-alpha-azido-2,3-dideoxy-2-beta-[3,4-dihydro-2,4-dioxo-5-methyl-1(2H)-pyrimidinyl]-D-arabinitol and 1,4-anhydro-3-alpha-azido-2,3-dideoxy-2-beta-[3,4-dihydro-2,-dioxo-1(2H)-pyrimidinyl]-D-arabinitol, conceptually new hydrolytically stable, optically active analogs of 3'-alpha-azido-3'-deoxythymidine (AZT) have been developed. These are among the first examples of regioisomeric analogs of AZT. The key synthetic steps and key intermediates are described. The generality aspects of the approaches are addressed.