3,4-Bis-O-(p-nitrobenzoyl)-D-xylal | 162934-25-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,4-Bis-O-(p-nitrobenzoyl)-D-xylal
• 英文别名: 3,4-di-O-p-nitro-benzoyl-D-xylal；3,4-di-O-p-nitrobenzoyl-D-xylal；di-O-(4-nitrobenzoyl)-D-xylal；di-p-nitrobenzoyl-D-xylal；[(3R,4R)-4-(4-nitrobenzoyl)oxy-3,4-dihydro-2H-pyran-3-yl] 4-nitrobenzoate
• CAS: 162934-25-0
• 化学式: C₁₉H₁₄N₂O₉
• 分子量: 414.328
• InChiKey: RUMCTFNPUPACMZ-IAGOWNOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  154
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3,4-Bis-O-(p-nitrobenzoyl)-D-xylal 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
• 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 为溶剂， 生成 3,4-Bis-O-(p-nitrobenzoyl)-D-xylal
  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

• Highly stereoselective addition of organozinc reagents to pentopyranose derived glycals: effect of protecting group and assignment of C-glycoside stereochemistry
  作者：Matthew J Cook、Matthew J.E Fletcher、Diane Gray、Peter J Lovell、Timothy Gallagher

  DOI：10.1016/j.tet.2004.04.004

  日期：2004.5

  The nucleophilic addition of ethyl 3-propionylzinc iodide to a variety of differently protected pentopyranose derived d-glycals 6a–g proceeds with good to high levels of diastereoselectivity to provide the corresponding β-C-glycosides 7. The stereochemistry of the para-nitrobenzoate derivative 7d has been confirmed by X-ray crystallography, and the stereochemistry of the other β-C-glycoside products

  将3-丙酰碘化乙基乙酯亲核加成到各种受不同保护的戊吡喃糖衍生的d-糖6a - g上，具有很好的非对映选择性，提供了相应的β- C-糖苷7。所述的立体化学对-nitrobenzoate衍生物7D已通过X射线晶体学确认，其它β-的立体化学Ç糖苷产品已关联到7d的。观察到的立体化学结果支持了Isobe的早期建议，即通空效应对于稳定和控制11代表的中间氧鎓物种的反应性很重要。
• 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）。
• 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.
• 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.