Acetic acid (2R,3S,4R,5S,6R)-4-azido-6-fluoro-5-hydroxy-2-methyl-tetrahydro-pyran-3-yl ester | 375824-26-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (2R,3S,4R,5S,6R)-4-azido-6-fluoro-5-hydroxy-2-methyl-tetrahydro-pyran-3-yl ester
• 英文别名: [(2R,3S,4R,5S,6R)-4-azido-6-fluoro-5-hydroxy-2-methyloxan-3-yl] acetate
• CAS: 375824-26-3
• 化学式: C₈H₁₂FN₃O₄
• 分子量: 233.199
• InChiKey: XJAURFLZZYQMRU-VDUCJHRSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  70.1
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3S,4R,5S,6R)-4-azido-6-fluoro-5-hydroxy-2-methyl-tetrahydro-pyran-3-yl ester 在 吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.62h， 生成 acetic acid 4-azido-5-{[17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxy]-diisopropyl-silanyloxy}-6-fluoro-2-methyl-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  β-Selective Glycosylations with Masked d-Mycosamine Precursors

  摘要：

  [GRAPHICS]Both an intramolecular aglycon delivery (IAD) method and an intermolecular S(N)2 displacement method were examined for beta -selective glycosylations of cholesterol with D-mycosamine. An anomeric sulfoxide, sulfide, selenide, and fluoride were all successfully used as glycosyl donors in IAD reactions. The alpha -bromo ketone 19 was synthesized from protected mycosamine and employed in an intermolecular S(N)2 glycosylation reaction, Both routes were successful for the model alcohol, cholesterol.

  DOI：

  10.1021/ol016617i
• 作为产物：
  描述：

  Acetic acid (2R,3S,4R,5S)-4-azido-5-hydroxy-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-3-yl ester 在 4 A molecular sieve 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以38%的产率得到Acetic acid (2R,3S,4R,5S,6R)-4-azido-6-fluoro-5-hydroxy-2-methyl-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  β-Selective Glycosylations with Masked d-Mycosamine Precursors

  摘要：

  [GRAPHICS]Both an intramolecular aglycon delivery (IAD) method and an intermolecular S(N)2 displacement method were examined for beta -selective glycosylations of cholesterol with D-mycosamine. An anomeric sulfoxide, sulfide, selenide, and fluoride were all successfully used as glycosyl donors in IAD reactions. The alpha -bromo ketone 19 was synthesized from protected mycosamine and employed in an intermolecular S(N)2 glycosylation reaction, Both routes were successful for the model alcohol, cholesterol.

  DOI：

  10.1021/ol016617i