Carbonic acid (2R,3S,5R)-2-hydroxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester methyl ester | 139705-30-9

• 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: Carbonic acid (2R,3S,5R)-2-hydroxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester methyl ester
• 英文别名: (2R,3S,5R)-2-(Hydroxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-YL)tetrahydrofuran-3-YL methyl carbonate；[(2R,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] methyl carbonate
• CAS: 139705-30-9
• 化学式: C₁₂H₁₆N₂O₇
• 分子量: 300.268
• InChiKey: MXCDUWJOJWWXAQ-DJLDLDEBSA-N

物化性质

• 密度：
  1.46±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  114
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  N-isopropylidene-O-methoxycarbonyl-hydroxylamine 、 beta-胸苷 以 四氢呋喃 为溶剂， 反应 30.0h， 以82%的产率得到Carbonic acid (2R,3S,5R)-2-hydroxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester methyl ester
  参考文献：
  名称：

  A novel and convenient route to 3'-carbonates from unprotected 2'-deoxy nucleosides through an enzymic reaction

  摘要：

  DOI：

  10.1021/jo00034a056

文献信息

• Lipase-mediated alkoxycarbonylation of nucleosides with oxime carbonates.
  作者：Francisco Morís、Vicente Gotor

  DOI：10.1016/s0040-4020(01)92279-3

  日期：1992.11

  5'-O-carbonates of ribonucleosides and 2'-deoxyribonucleosides could be obtained by enzymatic alkoxycarbonylation with SP 435 lipase (from Candida antarctica) and oxime carbonates, which are easily prepared from chloroformates. Ribonucleosides gave as result two kind of 5'-O-carbonates depending on whether alkoxy or acetone oxime moiety acted as the leaving group. In the case of 2-deoxynucleosides, the leaving group was always the acetonoxime moiety, giving rise to regioselective formation of the corresponding 5'-O-alkyl carbonates, together with small amounts of 3'-O-regiosiomer and diacylated compounds.