1-<5'-O-(tert-Butyldimethylsilyl)-3'-O-crotonyl-2'-O-<(imidazol-1-yl)thiocarbonyl>-β-D-ribofuranosyl>uracil

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 1-<5'-O-(tert-Butyldimethylsilyl)-3'-O-crotonyl-2'-O-<(imidazol-1-yl)thiocarbonyl>-β-D-ribofuranosyl>uracil
• 英文别名: [(2R,3R,4R,5R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-(2,4-dioxopyrimidin-1-yl)-4-(imidazole-1-carbothioyloxy)oxolan-3-yl] (E)-but-2-enoate
• 化学式: C₂₃H₃₂N₄O₇SSi
• 分子量: 536.681
• InChiKey: RYWVBXUJMMIPCQ-PLPBOLSDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.36
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  153
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1-<5'-O-(tert-Butyldimethylsilyl)-3'-O-crotonyl-2'-O-<(imidazol-1-yl)thiocarbonyl>-β-D-ribofuranosyl>uracil 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 反应 24.0h， 以20%的产率得到1-<5'-O-(tert-Butyldimethylsilyl)-2'-C-<(R)carboxyethylmethyl>-2'-deoxy-β-D-ribofuranosyl>uracil 3',2'-γ-lactone
  参考文献：
  名称：

  Stereospecific Synthesis and NMR Conformational Studies of .gamma.-Butyrolactones of Nucleosides as Chiral Synthons for the Preparation of 2'-C- and 3'-C-Branched-Chain Nucleosides

  摘要：

  A stereoselective method is described for the synthesis of [3.3.0] fused lactones (gamma-butyrolactones) of ribonucleosides at the 2' and 3' positions of the furanose ring by intramolecular addition of radicals onto the alpha-position of alpha,beta-unsaturated esters. A new chiral center is formed at an off-template site of the ribofuranose ring, with good diastereoselectivity. These gamma-butyrolactones of nucleosides are useful chiral synthons for the preparation of branched-chain nucleosides.;Opening of the lactone ring afforded highly functionalized 2'-C- and 3'-C-branched-chain nucleosides which are difficult to synthesize by currently available methods. Conformational analysis of the gamma-butyrolactones of nucleosides has indicated an unusual ribose ring conformation, probably induced by the fused gamma-lactone ring.

  DOI：

  10.1021/jo00104a021
• 作为产物：
  描述：

  巴豆酸 、 N,N'-硫羰基二咪唑 、 5'-O-(tert-butyldimethylsilyl)uridine 在 三正丁胺 、 2-氯-1-甲基吡啶碘化物 作用下， 生成 1-<5'-O-(tert-Butyldimethylsilyl)-3'-O-crotonyl-2'-O-<(imidazol-1-yl)thiocarbonyl>-β-D-ribofuranosyl>uracil 、 1-<5'-O-(tert-Butyldimethylsilyl)-2'-O-crotonyl-3'-O-<(imidazol-1-yl)thiocarbonyl>-β-D-ribofuranosyl>uracil
  参考文献：
  名称：

  Stereospecific Synthesis and NMR Conformational Studies of .gamma.-Butyrolactones of Nucleosides as Chiral Synthons for the Preparation of 2'-C- and 3'-C-Branched-Chain Nucleosides

  摘要：

  A stereoselective method is described for the synthesis of [3.3.0] fused lactones (gamma-butyrolactones) of ribonucleosides at the 2' and 3' positions of the furanose ring by intramolecular addition of radicals onto the alpha-position of alpha,beta-unsaturated esters. A new chiral center is formed at an off-template site of the ribofuranose ring, with good diastereoselectivity. These gamma-butyrolactones of nucleosides are useful chiral synthons for the preparation of branched-chain nucleosides.;Opening of the lactone ring afforded highly functionalized 2'-C- and 3'-C-branched-chain nucleosides which are difficult to synthesize by currently available methods. Conformational analysis of the gamma-butyrolactones of nucleosides has indicated an unusual ribose ring conformation, probably induced by the fused gamma-lactone ring.

  DOI：

  10.1021/jo00104a021

文献信息

• Stereospecific Synthesis and NMR Conformational Studies of .gamma.-Butyrolactones of Nucleosides as Chiral Synthons for the Preparation of 2'-C- and 3'-C-Branched-Chain Nucleosides
  作者：Sonsoles Velazquez、Maria Luisa Jimeno、Sophie Huss、Jan Balzarini、Maria-Jose Camarasa

  DOI：10.1021/jo00104a021

  日期：1994.12

  A stereoselective method is described for the synthesis of [3.3.0] fused lactones (gamma-butyrolactones) of ribonucleosides at the 2' and 3' positions of the furanose ring by intramolecular addition of radicals onto the alpha-position of alpha,beta-unsaturated esters. A new chiral center is formed at an off-template site of the ribofuranose ring, with good diastereoselectivity. These gamma-butyrolactones of nucleosides are useful chiral synthons for the preparation of branched-chain nucleosides.;Opening of the lactone ring afforded highly functionalized 2'-C- and 3'-C-branched-chain nucleosides which are difficult to synthesize by currently available methods. Conformational analysis of the gamma-butyrolactones of nucleosides has indicated an unusual ribose ring conformation, probably induced by the fused gamma-lactone ring.