1-<5'-O-(tert-Butyldimethylsilyl)-2',3'-dideoxy-2'-C-<2''-phenyl-1''-(N-isobutylcarbamoyl)-1''(R)-ethyl>-β-D-ribofuranosyl>uracil | 1027158-14-0

• 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)-2',3'-dideoxy-2'-C-<2''-phenyl-1''-(N-isobutylcarbamoyl)-1''(R)-ethyl>-β-D-ribofuranosyl>uracil
• 英文别名: (2S)-2-[(2R,3S,5S)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-2-(2,4-dioxopyrimidin-1-yl)oxolan-3-yl]-N-(2-methylpropyl)-3-phenylpropanamide
• CAS: 1027158-14-0
• 化学式: C₂₈H₄₃N₃O₅Si
• 分子量: 529.752
• InChiKey: PWIJXDQBZDSGLW-TUGCOKMYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.09
• 重原子数：
  37
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  97
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-<5'-O-(tert-Butyldimethylsilyl)-2',3'-dideoxy-2'-C-<2''-phenyl-1''-(N-isobutylcarbamoyl)-1''(R)-ethyl>-β-D-ribofuranosyl>uracil 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 0.75h， 以95%的产率得到1-<2',3'-Dideoxy-2'-C-<2''-phenyl-1''-(N-isobutylcarbamoyl)-1''(R)-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 、 三氯化铝 、 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 1,2-二氯乙烷 、 甲苯 、 苯 为溶剂， 反应 52.0h， 生成 1-<5'-O-(tert-Butyldimethylsilyl)-2',3'-dideoxy-2'-C-<2''-phenyl-1''-(N-isobutylcarbamoyl)-1''(R)-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

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.