(2R,4S,5S,6R)-4-azido-2-bromo-5-[tert-butyl(dimethyl)silyl]oxy-6-methyloxan-3-one | 375824-48-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (2R,4S,5S,6R)-4-azido-2-bromo-5-[tert-butyl(dimethyl)silyl]oxy-6-methyloxan-3-one
• CAS: 375824-48-9
• 化学式: C₁₂H₂₂BrN₃O₃Si
• 分子量: 364.314
• InChiKey: NBEXGOABVISQPO-OYBPUVFXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.76
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  49.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,4S,5S,6R)-4-azido-2-bromo-5-[tert-butyl(dimethyl)silyl]oxy-6-methyloxan-3-one 在 3 A molecular sieve 、 propanedithol 、 四丁基氟化铵 、 三乙胺 、 silver carbonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 144.42h， 生成 N-[(2R,3S,4S,5S,6R)-2-[[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-3,5-dihydroxy-6-methyloxan-4-yl]acetamide
  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：

  (3S,4S,5S,6R)-4-Azido-6-methyl-tetrahydro-pyran-2,3,5-triol 在 吡啶 、 2,6-二甲基吡啶 、 盐酸 、 4-二甲氨基吡啶 、 sodium hydroxide 、 4 A molecular sieve 、 三氟化硼乙醚 、 4-甲基苯磺酸吡啶 、 一溴化碘 、 三氟乙酸酐 、 1,1,3,3-四甲基脲 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 101.74h， 生成 (2R,4S,5S,6R)-4-azido-2-bromo-5-[tert-butyl(dimethyl)silyl]oxy-6-methyloxan-3-one
  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

文献信息

• β-Selective Glycosylations with Masked <scp>d</scp>-Mycosamine Precursors
  作者：Garrick K. Packard、Scott D. Rychnovsky

  DOI：10.1021/ol016617i

  日期：2001.10.1

  [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.