1,2-dideoxy-1-(3-pyridyl)-β-D-ribofuranose | 116003-76-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2-dideoxy-1-(3-pyridyl)-β-D-ribofuranose
• 英文别名: 1β-(pyridin-3-yl)-1,2-dideoxy-D-ribofuranose；1,2-dideoxy-β-1-(3-pyridyl)-D-ribofuranose；(2R,3S,5R)-2-(hydroxymethyl)-5-pyridin-3-yloxolan-3-ol
• CAS: 116003-76-0
• 化学式: C₁₀H₁₃NO₃
• 分子量: 195.218
• InChiKey: QHGIRHSVGCYZGS-IVZWLZJFSA-N

物化性质

• 沸点：
  415.8±45.0 °C(Predicted)
• 密度：
  1.278±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  62.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4,4'-双甲氧基三苯甲基氯 、 1,2-dideoxy-1-(3-pyridyl)-β-D-ribofuranose 以 吡啶 为溶剂， 反应 7.0h， 以89%的产率得到5'-O-(dimethoxytrityl)-1,2-dideoxy-1-(3-pyridyl)-D-ribofuranose
  参考文献：
  名称：

  A metallo base-pair incorporating a terpyridyl-like motif: bipyridyl-pyrimidinone·Ag(i)·4-pyridine

  摘要：

  报道了一种几何独特的金属碱基对模体的设计和表征。

  DOI：

  10.1039/b709291a
• 作为产物：
  描述：

  (2R,3S)-5,5-bis(ethylthio)pentane-1,2,3-triol 在 正丁基锂 、 碘 、 trityl tetrafluoroborate 、 sodium hydride 、 碳酸氢钠 、 溶剂黄146 、 N,N-二异丙基乙胺 作用下， 以 吡啶 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 11.84h， 生成 1,2-dideoxy-1-(3-pyridyl)-β-D-ribofuranose
  参考文献：
  名称：

  Eaton, Michael A. W.; Millican, T. Andrew; Mann, John, Journal of the Chemical Society. Perkin transactions I, 1988, p. 545 - 548

  摘要：

  DOI：

文献信息

• Modular and Practical Synthesis of 6-Substituted Pyridin-3-yl C-Nucleosides
  作者：Nicolas Joubert、Radek Pohl、Blanka Klepetářová、Michal Hocek

  DOI：10.1021/jo0709504

  日期：2007.8.31

  A novel modular and practical methodology for preparation of 6-substituted pyridin-3-yl C-nucleosides was developed. The Heck reaction of 2-chloro-5-iodopyridine with a 3'-TBDMS-protected glycal gave a 6-chloropyridin-3-yl nucleoside analogue, which was then desilylated, selectively reduced, and reprotected to give the TBDMS-protected 6-chloropyridin-3-yl C-2'-deoxyribonucleoside as a pure beta-anomer in a total yield of 39% over four steps. This key intermediate was then subjected to a series of palladium-catalyzed cross-coupling reactions, aminations, and alkoxylations to give a series of protected 1 beta-(6-alkyl-, 6-aryl-, 6-hetaryl, 6-amino-, and 6-tert-butoxypyridin-3-yl)-2'-deoxyribonucleosides. 6-Unsubstituted pyridin-3-yl C-nucleoside was prepared by catalytic hydrogenation of the chloro derivative and 6-oxopyridine C-nucleoside by treatment of the 6-tert-butoxy derivative with TFA. Deprotection of all the silylated nucleosides by Et3N center dot 3HF gave a series of free C-nucleosides (10 examples).
• A metallo base-pair incorporating a terpyridyl-like motif: bipyridyl-pyrimidinone·Ag(i)·4-pyridine
  作者：Dongwon Shin、Christopher Switzer

  DOI：10.1039/b709291a

  日期：——

  The design and characterization of a geometrically unique, metallo base-pair motif is reported.

  报道了一种几何独特的金属碱基对模体的设计和表征。
• Eaton, Michael A. W.; Millican, T. Andrew; Mann, John, Journal of the Chemical Society. Perkin transactions I, 1988, p. 545 - 548
  作者：Eaton, Michael A. W.、Millican, T. Andrew、Mann, John

  DOI：——

  日期：——