1-(2,3-dideoxy-α-D-glycero-pent-2-enopyranosyl)uracil | 169514-13-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1-(2,3-dideoxy-α-D-glycero-pent-2-enopyranosyl)uracil
• 英文别名: 1-[(3S,6S)-3-hydroxy-3,6-dihydro-2H-pyran-6-yl]pyrimidine-2,4-dione
• CAS: 169514-13-0
• 化学式: C₉H₁₀N₂O₄
• 分子量: 210.189
• InChiKey: IASWMJQGSJXYNC-XPUUQOCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  78.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(2,3-dideoxy-α-D-glycero-pent-2-enopyranosyl)uracil 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 生成 (2',3'-Dideoxy-α-D-glycero-pentopyranosyl)uracil
  参考文献：
  名称：

  Easy Synthesis and Different Conformational Behavior of Purine and Pyrimidine .beta.-D-glycero-Pent-2'-enopyranosyl Nucleosides

  摘要：

  Condensation of 3,4-bis-O-(p-nitrobenzoyl)-D-xylal with purines and pyrimidines (A, C, 6-chloropurine, G, T, U) without externally added acid catalyst leads to the 2',3'-unsaturated pentopyranosyl nucleosides in preparatively acceptable yields of both beta and alpha anomers and near complete suppression of formation of the 3'-substituted 1',2'-unsaturated regioisomers. Anomeric configurations of these analogues of nucleosides have been established for the 4'-O-deprotected derivatives by way of C-13 NMR. In all nine anomeric pairs the signals of the carbon atoms C-5' in alpha anomers are shifted upfield when compared with the corresponding signals of the beta anomers. Coupling constants J(4'5'ax) indicate pseudoaxial positions of purines in 33-40, 45, and 46. This is rationalized in terms of a pi-o*(c-1'-N-9) resonance and represents a case where aglycons occupy pseudoaxial positions via a mechanism'different than the anomeric effect. The same coupling constants of the alpha-pyrimidines 30, 32, 42, and 44 indicate H-4(0)<->H-0(4) equilibrium with a marginal preference toward the H-0(4) form, whereas the beta-pyrimidines 29, 31, 41, and 43 show a preference toward H-0(4) probably due to steric interactions.

  DOI：

  10.1021/jo00129a035
• 作为产物：
  描述：

  <4'-O-(p-Nitrobenzoyl)-2',3'-dideoxy-α-D-glycero-pent-2'-enopyranosyl>uracil 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 1-(2,3-dideoxy-α-D-glycero-pent-2-enopyranosyl)uracil
  参考文献：
  名称：

  Easy Synthesis and Different Conformational Behavior of Purine and Pyrimidine .beta.-D-glycero-Pent-2'-enopyranosyl Nucleosides

  摘要：

  Condensation of 3,4-bis-O-(p-nitrobenzoyl)-D-xylal with purines and pyrimidines (A, C, 6-chloropurine, G, T, U) without externally added acid catalyst leads to the 2',3'-unsaturated pentopyranosyl nucleosides in preparatively acceptable yields of both beta and alpha anomers and near complete suppression of formation of the 3'-substituted 1',2'-unsaturated regioisomers. Anomeric configurations of these analogues of nucleosides have been established for the 4'-O-deprotected derivatives by way of C-13 NMR. In all nine anomeric pairs the signals of the carbon atoms C-5' in alpha anomers are shifted upfield when compared with the corresponding signals of the beta anomers. Coupling constants J(4'5'ax) indicate pseudoaxial positions of purines in 33-40, 45, and 46. This is rationalized in terms of a pi-o*(c-1'-N-9) resonance and represents a case where aglycons occupy pseudoaxial positions via a mechanism'different than the anomeric effect. The same coupling constants of the alpha-pyrimidines 30, 32, 42, and 44 indicate H-4(0)<->H-0(4) equilibrium with a marginal preference toward the H-0(4) form, whereas the beta-pyrimidines 29, 31, 41, and 43 show a preference toward H-0(4) probably due to steric interactions.

  DOI：

  10.1021/jo00129a035

文献信息

• Synthesis, Antiviral and Cytostatic Evaluation of Unsaturated Exomethylene and Keto D&amp;hyphen;Lyxopyranonucleoside Analogues
  作者：Niki Tzioumaki、Evangelia Tsoukala、Stella Manta、George Agelis、Jan Balzarini、Dimitri Komiotis

  DOI：10.1002/ardp.200900004

  日期：2009.6

  group on the biological activity of the target molecules. Compounds 7a, b, 8a, b, and 13a, b were evaluated for their antiviral and cytostatic activity using several virus strains and cell lines. Whereas no marked antiviral activity was noticed, 13a and 13b showed a cytostatic activity that ranged between 7 and 23 μM for 13a and 26 and 38 μM for 13b against murine leukemia L1210, human lymphocyte Molt4/C8

  本报告描述了作为潜在生物活性剂的不饱和外亚甲基lyxopyranonucleoside 类似物的合成。市售的 1,2,3,4-四-O-乙酰-α-D-lyxopyranose 1 分别与甲硅烷基化胸腺嘧啶和尿嘧啶缩合，脱乙酰和缩醛得到 1-(2,3-O-异亚丙基-α- D-lyxopyranosyl)thymine 4a 和 1-(2,3-O-isopropylidene-α-D-lyxopyranosyl)uracil 4b。新的衍生物 1-(2,3,4-trideoxy-4-methylene-α-pent-2-enopyranosyl)thymine 8a 和 1-(2,3,4-trideoxy-4-methylene-α-pent-2-为了阐明2',3'-不饱和度的影响并阐明酮基和外亚甲基之间的差异，通过两种不同的关键中间体7a、b和13a、b制备了烯吡喃基）尿嘧啶8b。目标分子。化合物
• Easy Synthesis and Different Conformational Behavior of Purine and Pyrimidine .beta.-D-glycero-Pent-2'-enopyranosyl Nucleosides
  作者：Bogdan Doboszewski、Norbert Blaton、Piet Herdewijn

  DOI：10.1021/jo00129a035

  日期：1995.12

  Condensation of 3,4-bis-O-(p-nitrobenzoyl)-D-xylal with purines and pyrimidines (A, C, 6-chloropurine, G, T, U) without externally added acid catalyst leads to the 2',3'-unsaturated pentopyranosyl nucleosides in preparatively acceptable yields of both beta and alpha anomers and near complete suppression of formation of the 3'-substituted 1',2'-unsaturated regioisomers. Anomeric configurations of these analogues of nucleosides have been established for the 4'-O-deprotected derivatives by way of C-13 NMR. In all nine anomeric pairs the signals of the carbon atoms C-5' in alpha anomers are shifted upfield when compared with the corresponding signals of the beta anomers. Coupling constants J(4'5'ax) indicate pseudoaxial positions of purines in 33-40, 45, and 46. This is rationalized in terms of a pi-o*(c-1'-N-9) resonance and represents a case where aglycons occupy pseudoaxial positions via a mechanism'different than the anomeric effect. The same coupling constants of the alpha-pyrimidines 30, 32, 42, and 44 indicate H-4(0)<->H-0(4) equilibrium with a marginal preference toward the H-0(4) form, whereas the beta-pyrimidines 29, 31, 41, and 43 show a preference toward H-0(4) probably due to steric interactions.
• Synthesis of the β-2',3'-Unsaturated Pentopyranosyl Nucleosides and Their 3'-Hydroxymethyl Congeners
  作者：Bogdan Doboszewski、Norbert Blaton、Piet Herdewijn

  DOI：10.1080/15257779508012371

  日期：1995.5.1

  Fusion of the glycal 3 and purines/pyrimidines without acid catalyst provides anomeric mixtures of the 2',3'-unsaturated pentopyranosyl nucleosides 4, which have been worked out to furnish the 3'-hydroxymethyl analogues, e.g. 5.