(2',3'-Dideoxy-α-D-glycero-pent-2'-enopyranosyl)-6-methoxypurine | 162934-37-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: (2',3'-Dideoxy-α-D-glycero-pent-2'-enopyranosyl)-6-methoxypurine
• 英文别名: (3S,6S)-6-(6-methoxypurin-9-yl)-3,6-dihydro-2H-pyran-3-ol
• CAS: 162934-37-4
• 化学式: C₁₁H₁₂N₄O₃
• 分子量: 248.241
• InChiKey: VKACAYJKYGSMBY-YUMQZZPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  82.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2',3'-Dideoxy-α-D-glycero-pent-2'-enopyranosyl)-6-methoxypurine 在 氨 作用下， 以 甲醇 为溶剂， 反应 10.0h， 以16%的产率得到(3S,6S)-6-(6-Amino-purin-9-yl)-3,6-dihydro-2H-pyran-3-ol
  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：

  3,4-二-乙酰基-D-木糖烯 在 吡啶 、 sodium methylate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.67h， 生成 (2',3'-Dideoxy-α-D-glycero-pent-2'-enopyranosyl)-6-methoxypurine
  参考文献：
  名称：

  β构型的2'，3'-不饱和戊吡喃糖基核苷的合成

  摘要：

  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）。

  DOI：

  10.1016/0040-4039(94)02466-o

文献信息

• 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）。
• 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.