1-<5'-O-(tert-Butyldimethylsilyl)-3'-C-<(S)carboxybenzylmethyl>-3'-deoxy-β-D-ribofuranosyl>uracil 2',3'-γ-lactone | 137410-66-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃类
• 英文名称: 1-<5'-O-(tert-Butyldimethylsilyl)-3'-C-<(S)carboxybenzylmethyl>-3'-deoxy-β-D-ribofuranosyl>uracil 2',3'-γ-lactone
• 英文别名: 1-[(3S,3aR,4S,6R,6aR)-3-benzyl-4-[[tert-butyl(dimethyl)silyl]oxymethyl]-2-oxo-3a,4,6,6a-tetrahydro-3H-furo[2,3-c]furan-6-yl]pyrimidine-2,4-dione
• CAS: 137410-66-3
• 化学式: C₂₄H₃₂N₂O₆Si
• 分子量: 472.613
• InChiKey: XUOFTZJKRZULNR-MIGBRYPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.86
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  94.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  异丁胺 、 1-<5'-O-(tert-Butyldimethylsilyl)-3'-C-<(S)carboxybenzylmethyl>-3'-deoxy-β-D-ribofuranosyl>uracil 2',3'-γ-lactone 在 三氯化铝 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 16.0h， 以62%的产率得到1-<5'-O-(tert-Butyldimethylsilyl)-3'-deoxy-3'-C-<2''-phenyl-1''-(N-isobutylcarbamoyl)-1''(S)-ethyl>-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
• 作为产物：
  描述：

  5'-O-(tert-butyldimethylsilyl)uridine 在 吡啶 、 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 反应 23.0h， 生成 1-<5'-O-(tert-Butyldimethylsilyl)-3'-C-<(S)carboxybenzylmethyl>-3'-deoxy-β-D-ribofuranosyl>uracil 2',3'-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

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.