3-fluoro-3-deoxy-6-O-(p-nitrobenzoyl)-1,2-O-isopropylidene-α-D-glucofuranose | 133473-70-8

• 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-fluoro-3-deoxy-6-O-(p-nitrobenzoyl)-1,2-O-isopropylidene-α-D-glucofuranose
• 英文别名: [(2R)-2-[(3aR,5R,6S,6aS)-6-fluoro-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-hydroxyethyl] 4-nitrobenzoate
• CAS: 133473-70-8
• 化学式: C₁₆H₁₈FNO₈
• 分子量: 371.319
• InChiKey: YPDMEGXYQBRXLI-WPLOAARJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.33
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  117.36
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  3-fluoro-3-deoxy-6-O-(p-nitrobenzoyl)-1,2-O-isopropylidene-α-D-glucofuranose 在 吡啶 、 sodium periodate 、 Dowex-50 (H+) resin 、 氢溴酸 、 碳酸氢钠 作用下， 以 二氯甲烷 为溶剂， 反应 22.0h， 生成 2-fluoro-2-deoxy-3-O-acetyl-5-O-(p-nitrobenzoyl)-D-arabinofuranosyl bromide
  参考文献：
  名称：

  Pyridine coenzyme analogs. 3. Synthesis of three NAD+ analogs containing a 2'-deoxy-2'-substituted nicotinamide arabinofuranosyl moiety

  摘要：

  A general method for the preparation of 2'-deoxy-2'-substituted arabino-nicotinamide-adenine dinucleotide (NAD) analogues is described. Starting from 1,2:5,6-di-O-isopropylidine-alpha-D-allofuranose, the 2'-amino-, 2'-azido-, and 2'-fluoro-arabino-NAD analogues have been prepared. We report an improved phosphorylation procedure for nicotinamide nucleosides using pyrophosphoryl chloride in m-cresol. The selective reduction of azido substituents by aqueous dithiothreitol (DTT) in the presence of the readily reducible nicotinamide moiety is also reported. With both the 2'-azido and the 2'-fluoro substituents the cis configuration predominates for the incoming nicotinamide, thus allowing the stereoselective formation of the beta anomer in high yield.

  DOI：

  10.1021/jo00011a029
• 作为产物：
  描述：

  3-deoxy-1,2;5,6-di-O-isopropylidene-3-fluoro-α-D-glucofuranose 在 吡啶 、 硫酸 作用下， 以 1,4-二氧六环 、 乙醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 3-fluoro-3-deoxy-6-O-(p-nitrobenzoyl)-1,2-O-isopropylidene-α-D-glucofuranose
  参考文献：
  名称：

  Pyridine coenzyme analogs. 3. Synthesis of three NAD+ analogs containing a 2'-deoxy-2'-substituted nicotinamide arabinofuranosyl moiety

  摘要：

  A general method for the preparation of 2'-deoxy-2'-substituted arabino-nicotinamide-adenine dinucleotide (NAD) analogues is described. Starting from 1,2:5,6-di-O-isopropylidine-alpha-D-allofuranose, the 2'-amino-, 2'-azido-, and 2'-fluoro-arabino-NAD analogues have been prepared. We report an improved phosphorylation procedure for nicotinamide nucleosides using pyrophosphoryl chloride in m-cresol. The selective reduction of azido substituents by aqueous dithiothreitol (DTT) in the presence of the readily reducible nicotinamide moiety is also reported. With both the 2'-azido and the 2'-fluoro substituents the cis configuration predominates for the incoming nicotinamide, thus allowing the stereoselective formation of the beta anomer in high yield.

  DOI：

  10.1021/jo00011a029

文献信息

• Jiang, Hong; Congleton, Johanna; Liu, Qun, Journal of the American Chemical Society, 2009, vol. 131, p. 1658 - 1659
  作者：Jiang, Hong、Congleton, Johanna、Liu, Qun、Merchant, Paolomi、Malavasi, Fabio、et al.

  DOI：——

  日期：——
• SLEATH, PAUL R.;HANDLON, ANTHONY L.;OPPENHEIMER, NORMAN J., J. ORG. CHEM., 56,(1991) N1, C. 3608-3613
  作者：SLEATH, PAUL R.、HANDLON, ANTHONY L.、OPPENHEIMER, NORMAN J.

  DOI：——

  日期：——