[(2R,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] N-aminocarbamate | 218269-68-2

• 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: [(2R,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] N-aminocarbamate
• CAS: 218269-68-2
• 化学式: C₁₁H₁₆N₄O₆
• 分子量: 300.271
• InChiKey: MSPLNSUXYAIABV-XLPZGREQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  143
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3'-tert-butyldimethylsilylthymidine 5'-carboxaldehyde 、 [(2R,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] N-aminocarbamate 在 甲酸 作用下， 以 甲醇 为溶剂， 以70%的产率得到
  参考文献：
  名称：

  Synthesis of novel carbazoyl linked pyrimidine-pyrimidine and pyrimidine-purine dinucleotide analogues

  摘要：

  The synthesis of two backbone modified dinucleotide analogues is described in which the natural phosphodiester linkage is replaced by a 3'-5' carbazoyl linkage. In both cases the bridge was formed through a coupling reaction between an appropriate 3'-carbazoyl nucleoside analogue and an aldehyde nucleoside derivative. It is noteworthy that starting nucleosides 4 could be common materials to obtain the 3'-carbazoyl nucleoside derivatives 2, by means of a simple, previously-described chemoenzymatic procedure, and the aldehyde nucleoside 3, by an oxidation reaction. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00009-x
• 作为产物：
  描述：

  ethenyl [(2R,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] carbonate 在 一水合肼 作用下， 以 1,4-二氧六环 为溶剂， 生成 [(2R,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] N-aminocarbamate
  参考文献：
  名称：

  Synthesis of novel carbazoyl linked pyrimidine-pyrimidine and pyrimidine-purine dinucleotide analogues

  摘要：

  The synthesis of two backbone modified dinucleotide analogues is described in which the natural phosphodiester linkage is replaced by a 3'-5' carbazoyl linkage. In both cases the bridge was formed through a coupling reaction between an appropriate 3'-carbazoyl nucleoside analogue and an aldehyde nucleoside derivative. It is noteworthy that starting nucleosides 4 could be common materials to obtain the 3'-carbazoyl nucleoside derivatives 2, by means of a simple, previously-described chemoenzymatic procedure, and the aldehyde nucleoside 3, by an oxidation reaction. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00009-x

文献信息

• Chemoenzymatic Synthesis of Novel 3‘- and 5‘-Carbazoyl Nucleoside Derivatives. Regioselective Preparation of 3‘- and 5‘-Alkylidencarbazoyl Nucleosides
  作者：Julia Magdalena、Susana Fernández、Miguel Ferrero、Vicente Gotor

  DOI：10.1021/jo981062z

  日期：1998.11.1

  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.
• Synthesis of novel carbazoyl linked pyrimidine-pyrimidine and pyrimidine-purine dinucleotide analogues
  作者：Julia Magdalena、Susana Fernández、Miguel Ferrero、Vicente Gotor

  DOI：10.1016/s0040-4039(99)00009-x

  日期：1999.2

  The synthesis of two backbone modified dinucleotide analogues is described in which the natural phosphodiester linkage is replaced by a 3'-5' carbazoyl linkage. In both cases the bridge was formed through a coupling reaction between an appropriate 3'-carbazoyl nucleoside analogue and an aldehyde nucleoside derivative. It is noteworthy that starting nucleosides 4 could be common materials to obtain the 3'-carbazoyl nucleoside derivatives 2, by means of a simple, previously-described chemoenzymatic procedure, and the aldehyde nucleoside 3, by an oxidation reaction. (C) 1999 Elsevier Science Ltd. All rights reserved.