2,2-Dimethyl-propionic acid (2R,3R,5S,6S)-6-ethoxy-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-pyran-2-ylmethyl ester | 192062-76-3

• 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: 2,2-Dimethyl-propionic acid (2R,3R,5S,6S)-6-ethoxy-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-pyran-2-ylmethyl ester
• 英文别名: thymin-1-yl(-2d)[pivaloyl(-6)]3-deoxy-D-lyxHex(a)-O-Et；[(2R,3R,5S,6S)-6-ethoxy-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxan-2-yl]methyl 2,2-dimethylpropanoate
• CAS: 192062-76-3
• 化学式: C₁₈H₂₈N₂O₇
• 分子量: 384.43
• InChiKey: HDGZTAFELKEMDZ-JLNYLFASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  114
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,2-Dimethyl-propionic acid (2R,3R,5S,6S)-6-ethoxy-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-pyran-2-ylmethyl ester 在 sodium hydroxide 作用下， 生成 1-((2S,3S,5R,6R)-2-Ethoxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-5-methyl-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Isonucleosides by Michael addition of pyrimidine bases on 2,6-disubstituted 2H-pyran-3(6H)-ones

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(97)00859-9
• 作为产物：
  描述：

  ethyl 6-O-(2,2-dimethyl-1-oxopropyl)-2,3-dideoxy-α-D-glycero-hex-2-enopyranosid-4-ulose 在 sodium tetrahydroborate 、 N,O-双三甲硅基乙酰胺 、 三氟甲磺酸三甲基硅酯 作用下， 反应 2.0h， 生成 2,2-Dimethyl-propionic acid (2R,3R,5S,6S)-6-ethoxy-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-pyran-2-ylmethyl ester
  参考文献：
  名称：

  Isonucleosides by Michael addition of pyrimidine bases on 2,6-disubstituted 2H-pyran-3(6H)-ones

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(97)00859-9