2,6-dibenzyloxy-5-methyl-3-methoxymethylpyridine | 138944-55-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,6-dibenzyloxy-5-methyl-3-methoxymethylpyridine
• 英文别名: 3-(methoxymethyl)-5-methyl-2,6-bis(phenylmethoxy)pyridine
• CAS: 138944-55-5
• 化学式: C₂₂H₂₃NO₃
• 分子量: 349.43
• InChiKey: LXIKQTQQSHSMIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.69
• 重原子数：
  26.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  40.58
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  哌喃 、 3,5-二氯-6-甲基-1,4-噁唑-2-酮 、 苯甲醇 生成 2,6-dibenzyloxy-4-hydroxymethyl-3-methylpyridine 、 2,6-dibenzyloxy-5-methyl-3-methoxymethylpyridine
  参考文献：
  名称：

  An approach to acyclo-1-deazathymidine c-nucleosides via 3,5-dichloro-6-methyl-2H-1,4-oxazin-2-one.

  摘要：

  An approach to the synthesis of acyclo-1-deazathymidine nucleosides is described. Diels-Alder reaction of 3,5-dichloro-6-methyl-2H-1,4-oxazin-2-one with acetylenic compounds 4 and 5 yielded the 3-[(tetrahydropyran-2-yl)oxy]methyl- and 3-bromomethyl-5-methyl-2,6-dichloropyridine intermediates 7 and 8. The bromomethyl group of compound 8 underwent easy substitution with the appropriate nucleophiles, permitting the introduction of acyclo sugar moieties. The resulting 3-substituted 2,6-dichloro-5-methyl pyridines 9a,b - precursors for some acyclo pyridine-C-nucleosides - were treated with sodium phenylmethoxide to afford 2,6-dibenzyloxpyridines 10a,b. Debenzylation using a palladium-strontium carbonate catalyst gave the unstable C-nucelosides 2a,b of the 6-hydroxy-1-H-pyridin-2-one type. A stable 6-hydroxy-1-H-pyridin-2-one 2c, exempt from benzylic oxygen, was obtained via cycloaddition of THP-protected 6-hydroxy-1-hexyne.

  DOI：

  10.1016/s0040-4020(01)96055-7

文献信息

• An approach to acyclo-1-deazathymidine c-nucleosides via 3,5-dichloro-6-methyl-2H-1,4-oxazin-2-one.
  作者：Lieven Meerpoel、Suzanne M. Toppet、Frans Compernolle、Georges J. Hoornaert

  DOI：10.1016/s0040-4020(01)96055-7

  日期：1991.1

  An approach to the synthesis of acyclo-1-deazathymidine nucleosides is described. Diels-Alder reaction of 3,5-dichloro-6-methyl-2H-1,4-oxazin-2-one with acetylenic compounds 4 and 5 yielded the 3-[(tetrahydropyran-2-yl)oxy]methyl- and 3-bromomethyl-5-methyl-2,6-dichloropyridine intermediates 7 and 8. The bromomethyl group of compound 8 underwent easy substitution with the appropriate nucleophiles, permitting the introduction of acyclo sugar moieties. The resulting 3-substituted 2,6-dichloro-5-methyl pyridines 9a,b - precursors for some acyclo pyridine-C-nucleosides - were treated with sodium phenylmethoxide to afford 2,6-dibenzyloxpyridines 10a,b. Debenzylation using a palladium-strontium carbonate catalyst gave the unstable C-nucelosides 2a,b of the 6-hydroxy-1-H-pyridin-2-one type. A stable 6-hydroxy-1-H-pyridin-2-one 2c, exempt from benzylic oxygen, was obtained via cycloaddition of THP-protected 6-hydroxy-1-hexyne.