isopropyl 2'-thymine-6-O-tert-butyldimethylsilyl-4-keto-2,3-dideoxy-α-D-erythro-hexopyranoside | 190974-14-2

• 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: isopropyl 2'-thymine-6-O-tert-butyldimethylsilyl-4-keto-2,3-dideoxy-α-D-erythro-hexopyranoside
• 英文别名: 1-[(2S,3S,6R)-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-oxo-2-propan-2-yloxyoxan-3-yl]-5-methylpyrimidine-2,4-dione
• CAS: 190974-14-2
• 化学式: C₂₀H₃₄N₂O₆Si
• 分子量: 426.585
• InChiKey: SFYGLXPZGWEPIG-LESCRADOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.52
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  isopropyl 2'-thymine-6-O-tert-butyldimethylsilyl-4-keto-2,3-dideoxy-α-D-erythro-hexopyranoside 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 0.25h， 以61%的产率得到1-[(2S,3S,6R)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-5-hydroxy-2-isopropoxy-tetrahydro-pyran-3-yl]-5-methyl-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  A Novel Route to PyrimidineIsodideoxynucleosidesviaMichael-Type Addition on Unsaturated Modified Sugars

  摘要：

  A short, stereocontrolled synthesis of isonucleosides is described. This approach is based on the Michael-Type addition of silylated uracil or thymine with an appropriate acceptor as pyranoside precursor. The alkylated products obtained allow carbonyl reduction, providing a straightforward way to prepare new sugar-modified nucleosides.

  DOI：

  10.1080/00397919708003388
• 作为产物：
  描述：

  isopropyl 2,3-dideoxy-α-D-erythro-hex-2-enopyranoside 在 4-二甲氨基吡啶 、 重铬酸吡啶 、 N,O-双三甲硅基乙酰胺 、 三氟甲磺酸三甲基硅酯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 52.0h， 生成 isopropyl 2'-thymine-6-O-tert-butyldimethylsilyl-4-keto-2,3-dideoxy-α-D-erythro-hexopyranoside
  参考文献：
  名称：

  A Novel Route to PyrimidineIsodideoxynucleosidesviaMichael-Type Addition on Unsaturated Modified Sugars

  摘要：

  A short, stereocontrolled synthesis of isonucleosides is described. This approach is based on the Michael-Type addition of silylated uracil or thymine with an appropriate acceptor as pyranoside precursor. The alkylated products obtained allow carbonyl reduction, providing a straightforward way to prepare new sugar-modified nucleosides.

  DOI：

  10.1080/00397919708003388

文献信息

• Isonucleosides by Michael addition of pyrimidine bases on 2,6-disubstituted 2H-pyran-3(6H)-ones
  作者：Natacha Prévost、Francis Rouessac

  DOI：10.1016/s0040-4039(97)00859-9

  日期：1997.6

  A short, stereocontrolled convergent synthesis of pyranosyl isonucleosides, based on a Michael type addition between a silylated pyrimidine base and an unsaturated pyran-3(6H)-one is described. Diastereomeric ratio are of 90/10 up to 100/0, providing a straightforward way to prepare new nucleosides analogues. (C) 1997 Published by Elsevier Science Ltd.
• A Novel Route to Pyrimidine<i>Iso</i>dideoxynucleosides<i>via</i>Michael-Type Addition on Unsaturated Modified Sugars
  作者：Natacha Prévost、Francis Rouessac

  DOI：10.1080/00397919708003388

  日期：1997.7

  A short, stereocontrolled synthesis of isonucleosides is described. This approach is based on the Michael-Type addition of silylated uracil or thymine with an appropriate acceptor as pyranoside precursor. The alkylated products obtained allow carbonyl reduction, providing a straightforward way to prepare new sugar-modified nucleosides.