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]-dimethyl-silanyloxy}-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-3-yl ester | 375824-32-1

• 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: 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]-dimethyl-silanyloxy}-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-3-yl ester
• CAS: 375824-32-1
• 化学式: C₄₃H₆₇N₃O₅SSi
• 分子量: 766.174
• InChiKey: UGKPZTBKBSWXJV-XLSHVJFPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.65
• 重原子数：
  53.0
• 可旋转键数：
  13.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  102.75
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  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]-dimethyl-silanyloxy}-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-3-yl ester 在 2,6-二叔丁基吡啶 、 4 A molecular sieve 、 三氟甲烷磺酸甲酯 、 水 、 4-甲基苯磺酸吡啶 作用下， 以 二氯甲烷 、 甲醇 为溶剂， 反应 92.5h， 以61%的产率得到[(2R,3S,4R,5S,6R)-4-azido-6-[[(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]-5-hydroxy-2-methyloxan-3-yl] acetate
  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 咪唑 、 4-二甲氨基吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.03h， 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]-dimethyl-silanyloxy}-2-methyl-6-phenylsulfanyl-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