acetic acid 4-azido-6-benzenesulfinyl-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-tetrahydro-pyran-3-yl ester | 375824-28-5

• 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-6-benzenesulfinyl-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-tetrahydro-pyran-3-yl ester
• CAS: 375824-28-5
• 化学式: C₄₃H₆₇N₃O₆SSi
• 分子量: 782.173
• InChiKey: UAAMUCFDYRKMEW-LGUCZRTCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.66
• 重原子数：
  54.0
• 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：
  119.82
• 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-6-benzenesulfinyl-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-tetrahydro-pyran-3-yl ester 在 2,6-二叔丁基吡啶 、 三氟甲磺酸酐 、 4 A molecular sieve 、 propanedithol 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 12.67h， 生成 (2R,3S,4S,5S,6R)-4-Amino-2-[(3S,8S,9S,10R,13R,14S,17R)-17-((R)-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]-6-methyl-tetrahydro-pyran-3,5-diol
  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-6-benzenesulfinyl-5-hydroxy-2-methyl-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 0.37h， 生成 acetic acid 4-azido-6-benzenesulfinyl-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-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