5'-O-(vinyloxy)carbonyl-2',3'-isopropylideneadenosine | 218269-92-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 5'-O-(vinyloxy)carbonyl-2',3'-isopropylideneadenosine
• 英文别名: [(3aR,4R,6R,6aR)-4-(6-aminopurin-9-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methyl ethenyl carbonate
• CAS: 218269-92-2
• 化学式: C₁₆H₁₉N₅O₆
• 分子量: 377.357
• InChiKey: HMTICLZQOOSXDM-IDTAVKCVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  133
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  5'-O-(vinyloxy)carbonyl-2',3'-isopropylideneadenosine 在 对甲苯磺酸 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 12.0h， 生成
  参考文献：
  名称：

  含有亚烷基咔唑基的核苷中1,2-缩酮的脱保护困难。

  摘要：

  显示了未保护的亚烷基咔唑基核苷衍生物8a-8d的合成。从容易获得的2'，3'-亚异丙基保护的核苷5a-5d的直接脱保护路径。由化学酶法制备的化合物没有在不影响C ＝ N键的情况下选择性切割缩酮功能。尝试的下一个选择是观察逆向合成途径中的先前化合物：2'，3'-保护的咔唑基核苷4。但是，在所有情况下，我们均未获得满意的结果。再往后退，化合物3a的水解使我们以定量收率得到了未保护的碳酸核苷9。利用该化合物，通过已知方法完成了向衍生物8的合成。

  DOI：

  10.1081/ncn-120006530
• 作为产物：
  描述：

  2',3'-异丙叉腺苷 、 丙酮O-<(乙烯氧基)羰基>肟 以 四氢呋喃 为溶剂， 以28.5%的产率得到5'-O-(acetoxime)carbonyl-2',3'-isopropylideneadenosine
  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

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.
• DIFFICULTIES IN THE DEPROTECTION OF 1,2-KETALS IN NUCLEOSIDES CONTAINING ALKYLIDENCARBAZOYL GROUPS
  作者：Julia Magdalena、Susana Fernández、Miguel Ferrero、Vicente Gotor

  DOI：10.1081/ncn-120006530

  日期：2002.4.15

  synthesis of unprotected alkylidencarbazoyl nucleoside derivatives 8a-8d is shown. A direct deprotection route from readily available 2',3'-isopropylidene protected nucleosides 5a-5d. prepared from a chemoenzymatic procedure, did not give the selective cleavage of the ketal function without affecting the C=N bond. The next option tried was to look at the previous compound in the retrosynthetic route: 2',3'-protected

  显示了未保护的亚烷基咔唑基核苷衍生物8a-8d的合成。从容易获得的2'，3'-亚异丙基保护的核苷5a-5d的直接脱保护路径。由化学酶法制备的化合物没有在不影响C ＝ N键的情况下选择性切割缩酮功能。尝试的下一个选择是观察逆向合成途径中的先前化合物：2'，3'-保护的咔唑基核苷4。但是，在所有情况下，我们均未获得满意的结果。再往后退，化合物3a的水解使我们以定量收率得到了未保护的碳酸核苷9。利用该化合物，通过已知方法完成了向衍生物8的合成。