1-(2,3-didesoxy-β-D-glyceropent-2-enopyranosyl)thymine | 119933-42-5

• 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-didesoxy-β-D-glyceropent-2-enopyranosyl)thymine
• 英文别名: 1-[(3S,6R)-3-hydroxy-3,6-dihydro-2H-pyran-6-yl]-5-methylpyrimidine-2,4-dione
• CAS: 119933-42-5
• 化学式: C₁₀H₁₂N₂O₄
• 分子量: 224.216
• InChiKey: GNXHILFBLCJQIR-JGVFFNPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 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-didesoxy-β-D-glyceropent-2-enopyranosyl)thymine 生成 1-(4-O-acetyl-2,3-didesoxy-β-D-3-glyceropent-2-enopyranosyl)thymine
  参考文献：
  名称：

  MIXAJLOV, S. N.;EFIMTSEVA, E. V., XIMIYA GETEROTSIKL. SOED.,(1988) N 7, 947-951

  摘要：

  DOI：
• 作为产物：
  描述：

  O,O-二(三甲基甲硅烷基)胸苷 在 sodium methylate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 1-(2,3-didesoxy-β-D-glyceropent-2-enopyranosyl)thymine
  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

• 3′-Deoxy-3′-hydroxymethyl-aldopentopyranosyl nucleoside synthesis. Part I
  作者：Bogdan Doboszewski、Norbert Blaton、Jef Rozenski、André De Bruyn、Piet Herdewijn

  DOI：10.1016/0040-4020(95)00211-p

  日期：1995.5

  A straightforward synthesis of 3′-deoxy-3′-hydroxymethyl-aldopentopyranosyl nucleosides is described starting from β-d-xylopyranosyl nucleosides. β-d-xylopyranosyl thymine 17a,b,c and uracil 17d are converted into the 4′-benzoylated derivatives 18a,b and further into the 2′,3′-enepyranosyl compounds 19b,c. A 3′-hydroxymethyl appendix has been introduced using a free-radical methodology to furnish 20a

  从β-d-吡喃吡喃糖基核苷开始描述了3'-脱氧-3'-羟甲基-醛基戊吡喃糖基核苷的直接合成。将β-d-吡喃喃喃糖基胸腺嘧啶17a，b，c和尿嘧啶17d转化为4′-苯甲酰化衍生物18a，b，并进一步转化为2′，3′-烯吡喃糖基化合物19b，c。已经使用自由基方法引入了3'-羟甲基附录来提供20a，b。反转4'-位置的构型产生靶核苷22a，b。X射线和1 H NMR构象分析证明了目标化合物中碱基部分的赤道取向。
• Synthesis of β configured 2′,3′-unsaturated pentopyranosyl nucleosides
  作者：Bodgan Doboszewski、Norbert Blaton、Piet Herdewijn

  DOI：10.1016/0040-4039(94)02466-o

  日期：1995.2

  of 3,4-di-O-p-nitrobenzoyl-D-xylal with heterocyclic bases in boiling DMF in the absence of externally added acid catalyst constitutes a convenient way to β configured 2′,3′-unsaturated pentopyranosyl nucleosides. Formation of the 3′-substituted products (without migration of a double bond) has been practically avoided.

  在没有外部添加的酸催化剂的情况下，在沸腾DMF中将3,4-二-O-硝基苯甲酰基-D-二甲苯基与杂环碱偶联，是构建β构型的2'，3'-不饱和戊吡喃糖基核苷的简便方法。实际上已经避免了形成3'-取代的产物（没有双键的迁移）。
• Synthesis of enantiomers of 3?,4?-seco-2?-desoxythymidine
  作者：S. N. Mikhailov、E. V. Efimtseva

  DOI：10.1007/bf00633175

  日期：1988.7
• Phosphonates Derivatives of 2',3'-Dideoxy-2',3'-didehydro-pentopyranosyl Nucleosides
  作者：María-Jesús Péarez-Péarez、Bogdan Doboszewski、Erik De Clercq、P. Herdewijn

  DOI：10.1080/15257779508012454

  日期：1995.5.1
• 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.