1β-(6-ethylpyridin-2-yl)-1,2-dideoxy-D-ribofuranose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1β-(6-ethylpyridin-2-yl)-1,2-dideoxy-D-ribofuranose
• 英文别名: (2R,3S,5R)-5-(6-ethylpyridin-2-yl)-2-(hydroxymethyl)oxolan-3-ol
• 化学式: C₁₂H₁₇NO₃
• 分子量: 223.272
• InChiKey: BIKYWIXDPAQTFX-QJPTWQEYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  62.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-deoxy-D-ribose 在 咪唑 、 四(三苯基膦)钯 、 正丁基锂 、 溴 、 triethylamine tris(hydrogen fluoride) 作用下， 以 四氢呋喃 、 正己烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 182.33h， 生成 1β-(6-ethylpyridin-2-yl)-1,2-dideoxy-D-ribofuranose
  参考文献：
  名称：

  New Modular and Efficient Approach to 6-Substituted Pyridin-2-yl C-Nucleosides

  摘要：

  A novel modular, efficient, and practical methodology of preparation of 6-substituted pyridin-2-yl C-nucleosides was developed. An addition of 2-lithio-6-bromopyridine 2b to TBDMS-protected 2-deoxyribonolactone 5 gave aduct 7 as an equilibrium mixture of anomeric hemiketals 1-(6-bromopyridin-2-yl)-1-hydroxynucleosides 7a, b and its open form 7c. Reduction of the adduct 7 with Et3SiH and BF3 center dot Et2O afforded the desired 6-bromonucleoside 8a as pure beta-anomer in a total yield of 32% over two steps from 5. Intermediate 8a was then subjected to a series of palladium catalyzed cross-coupling reactions and aminations to give a series of protected 1 beta-(6-alkyl-, 6-aryl-, and 6-aminopyridin-2-yl)-2-deoxyribonucleosides 9. Catalytic hydrogenation of 8a gave an unsubstituted pyridine C-nucleoside, and diazotative oxodeamination of 6-aminopyridine nucleoside 9f by isopentyl nitrite in acetic acid gave 6-oxopyridine nucleoside 10i. Deprotection of silylated nucleosides 9 by Et3N center dot 3HF gave a series of free C-nucleosides 10.

  DOI：

  10.1021/jo061080d

文献信息

• New Modular and Efficient Approach to 6-Substituted Pyridin-2-yl C-Nucleosides
  作者：Milan Urban、Radek Pohl、Blanka Klepetářová、Michal Hocek

  DOI：10.1021/jo061080d

  日期：2006.9.1

  A novel modular, efficient, and practical methodology of preparation of 6-substituted pyridin-2-yl C-nucleosides was developed. An addition of 2-lithio-6-bromopyridine 2b to TBDMS-protected 2-deoxyribonolactone 5 gave aduct 7 as an equilibrium mixture of anomeric hemiketals 1-(6-bromopyridin-2-yl)-1-hydroxynucleosides 7a, b and its open form 7c. Reduction of the adduct 7 with Et3SiH and BF3 center dot Et2O afforded the desired 6-bromonucleoside 8a as pure beta-anomer in a total yield of 32% over two steps from 5. Intermediate 8a was then subjected to a series of palladium catalyzed cross-coupling reactions and aminations to give a series of protected 1 beta-(6-alkyl-, 6-aryl-, and 6-aminopyridin-2-yl)-2-deoxyribonucleosides 9. Catalytic hydrogenation of 8a gave an unsubstituted pyridine C-nucleoside, and diazotative oxodeamination of 6-aminopyridine nucleoside 9f by isopentyl nitrite in acetic acid gave 6-oxopyridine nucleoside 10i. Deprotection of silylated nucleosides 9 by Et3N center dot 3HF gave a series of free C-nucleosides 10.