Hvjzyezhwlzskp-qcnrffrdsa- | 146457-41-2

• 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: Hvjzyezhwlzskp-qcnrffrdsa-
• 英文别名: [(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl (propan-2-ylideneamino) carbonate
• CAS: 146457-41-2
• 化学式: C₁₃H₁₇N₃O₈
• 分子量: 343.293
• InChiKey: HVJZYEZHWLZSKP-QCNRFFRDSA-N

物化性质

• 密度：
  1.64±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  147
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  Hvjzyezhwlzskp-qcnrffrdsa- 在 一水合肼 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 以100%的产率得到[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl N-aminocarbamate
  参考文献：
  名称：

  Chemoenzymatic Synthesis of Novel 3‘- and 5‘-Carbazoyl Nucleoside Derivatives. Regioselective Preparation of 3‘- and 5‘-Alkylidencarbazoyl Nucleosides

  摘要：

  A chemoenzymatic procedure is described for the synthesis of 3'- and 5'-carbazoyl nucleoside derivatives 12a,b, 13a,b, 14b,c, and 30b, and these are prepared for the first time. This process involves the regioselective enzymatic alkoxycarbonylation of nucleosides and the subsequent transformation with hydrazine into novel carbazoyl nucleoside derivatives. Taking into account previously reported data (relative to nucleoside, hydrazone, carbazate, and aryloxyphenoxypropionate derivatives), 3'-alkylidencarbazoyl 2'-deoxynucleosides 15a,b-18a,b, 5'-alkylidencarbazoyl 2'-deoxynucleosides 19a,b-22a,b, 5'-alkylidencarbazoyl ribonucleosides of uridine 23c-26c, and 5'-alkylidencarbazoyl-2',3'-isopropylideneadenosine 31b-34b emerge as interesting targets since they combine structural features found in both therapeutic nucleoside derivatives and fungicide/herbicide nucleoside analogues.

  DOI：

  10.1021/jo981062z
• 作为产物：
  描述：

  丙酮O-<(乙烯氧基)羰基>肟 、 尿嘧啶核苷 以 四氢呋喃 为溶剂， 反应 24.0h， 以62%的产率得到Carbonic acid (2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl ester vinyl ester
  参考文献：
  名称：

  嘌呤和嘧啶3'-氨基-3'-脱氧-和3'-氨基-2'，3'-二脱氧木糖核苷的合成。

  摘要：

  提出了获得3'-氨基木糖核苷13a，b和17a，b的一般方法。合成方案基于在核苷的3'活化位置的5'定向分子内亲核取代。进入的基团到达该位置的途径是从核苷的最受阻表面区域性和立体选择性地发生的。提出的方法学适用于核糖核苷和2'-脱氧核糖核苷，无论它们的碱基是否已硝化。

  DOI：

  10.1021/jo9606259

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.
• Synthesis of 5′-O-and 3′-O-nucleoside carbamates
  作者：Luis F. García-Alles、Vicente Gotor

  DOI：10.1016/0040-4020(94)00948-t

  日期：1995.1

  The two step synthesis of 5'-O- and 3'-O-(N-alkylcarbamoyl)-nucleosides is described. The key step is the enzymatic synthesis of 5'-O- or 3'-O-alkoxycarbonylnucleoside in a regioselective way. In a second aminolysis step these carbonates yield the corresponding urethanes. This methodology allows to assemble aminoalcohols and L-amino acids to 2'-deoxynucleosides.

表征谱图