(2R,3S,4R,5S,6R)-4-azido-5-[tert-butyl(dimethyl)silyl]oxy-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]-6-methyloxan-3-ol | 375824-53-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: (2R,3S,4R,5S,6R)-4-azido-5-[tert-butyl(dimethyl)silyl]oxy-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]-6-methyloxan-3-ol
• CAS: 375824-53-6
• 化学式: C₃₉H₆₉N₃O₄Si
• 分子量: 672.08
• InChiKey: ZPRAIMJUZMGWRX-REIAYPNQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.59
• 重原子数：
  47
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  62.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,3S,4R,5S,6R)-4-azido-5-[tert-butyl(dimethyl)silyl]oxy-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]-6-methyloxan-3-ol 在 propanedithol 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 96.0h， 生成
  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：

  (3aS,5R,6S,7S,7aS)-7-Azido-2,2,5-trimethyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6-ol 在 吡啶 、 2,6-二甲基吡啶 、 盐酸 、 4-二甲氨基吡啶 、 sodium hydroxide 、 3 A molecular sieve 、 4 A molecular sieve 、 三氟化硼乙醚 、 4-甲基苯磺酸吡啶 、 一溴化碘 、 silver carbonate 、 三氟乙酸酐 、 1,1,3,3-四甲基脲 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 97.74h， 生成 (2R,3S,4R,5S,6R)-4-azido-5-[tert-butyl(dimethyl)silyl]oxy-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]-6-methyloxan-3-ol
  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.