ethenyl [(2R,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] carbonate | 139705-36-5

• 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: ethenyl [(2R,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] carbonate
• CAS: 139705-36-5
• 化学式: C₁₃H₁₆N₂O₇
• 分子量: 312.279
• InChiKey: JOKXSKONZYDKNO-IVZWLZJFSA-N

物化性质

• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 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：

  ethenyl [(2R,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] carbonate 在 对甲苯磺酸 、 一水合肼 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 4.5h， 生成 N'-[1-Phenyl-meth-(E)-ylidene]-hydrazinecarboxylic acid (2R,3S,5R)-2-hydroxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester
  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 、 beta-胸苷 在 PS lipase 作用下， 以 四氢呋喃 为溶剂， 以80%的产率得到ethenyl [(2R,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] carbonate
  参考文献：
  名称：

  化学酶法合成2'-脱氧核苷氨基甲酸酯

  摘要：

  以两步法合成2′-脱氧核苷5′-和3′-（N-烷基）氨基甲酸酯，用脂肪酶催化第一区域选择性乙烯基氧羰基化步骤。

  DOI：

  10.1016/s0040-4039(00)73746-4

文献信息

• A novel and convenient route to 3'-carbonates from unprotected 2'-deoxy nucleosides through an enzymic reaction
  作者：Franciso Moris、Vicente Gotor

  DOI：10.1021/jo00034a056

  日期：1992.4
• 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.
• 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.
• Chemo-enzymatic synthesis of 2′-deoxynucleoside urethanes
  作者：Luis F. García-Alles、Francisco Morís、Vicente Gotor

  DOI：10.1016/s0040-4039(00)73746-4

  日期：1993.9

  2′-Deoxynucleoside 5′- and 3′-(N-alkyl) carbamates were synthesized in a two step procedure, asing lipases to catalyze the first regioselective vinyloxycarbonylation step.

  以两步法合成2′-脱氧核苷5′-和3′-（N-烷基）氨基甲酸酯，用脂肪酶催化第一区域选择性乙烯基氧羰基化步骤。