1β-(6-chloropyridin-3-yl)-1,2-dideoxy-D-ribofuranose | 950830-39-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1β-(6-chloropyridin-3-yl)-1,2-dideoxy-D-ribofuranose
• 英文别名: (2R,3S,5R)-5-(6-chloropyridin-3-yl)-2-(hydroxymethyl)oxolan-3-ol
• CAS: 950830-39-4
• 化学式: C₁₀H₁₂ClNO₃
• 分子量: 229.663
• InChiKey: JSGKYNJABNMALQ-DJLDLDEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  15
• 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：

  1β-(6-chloropyridin-3-yl)-1,2-dideoxy-D-ribofuranose 在 四(三苯基膦)钯 咪唑 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 1β-(6-ethylpyridin-3-yl)-1,2-dideoxy-3,5-di-O-(t-butyldimethylsilyl)-D-ribofuranose
  参考文献：
  名称：

  Modular and Practical Synthesis of 6-Substituted Pyridin-3-yl C-Nucleosides

  摘要：

  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).

  DOI：

  10.1021/jo0709504
• 作为产物：
  描述：

  {(2R,3S)-3-[(tert-butyldimethylsilyl)oxy]-2,3-dihydrofuran-2-yl}methanol 在 palladium diacetate 三苯胂 、 三乙酰氧基硼氢化钠 、 溶剂黄146 、 triethylamine tris(hydrogen fluoride) 、 silver carbonate 作用下， 以 四氢呋喃 、 氯仿 、 乙腈 为溶剂， 反应 16.16h， 生成 1β-(6-chloropyridin-3-yl)-1,2-dideoxy-D-ribofuranose
  参考文献：
  名称：

  Modular and Practical Synthesis of 6-Substituted Pyridin-3-yl C-Nucleosides

  摘要：

  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).

  DOI：

  10.1021/jo0709504

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).