[(2R,3S,4R,5S,6R)-5-acetamido-3,4-diacetyloxy-6-[(2S)-3-[(2S,5R,6S,9R)-4,9-dimethyl-3-oxo-6-propan-2-yl-1,4-diazaspiro[4.5]decan-2-yl]-2-hydroxypropyl]oxan-2-yl]methyl acetate | 341013-98-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2R,3S,4R,5S,6R)-5-acetamido-3,4-diacetyloxy-6-[(2S)-3-[(2S,5R,6S,9R)-4,9-dimethyl-3-oxo-6-propan-2-yl-1,4-diazaspiro[4.5]decan-2-yl]-2-hydroxypropyl]oxan-2-yl]methyl acetate
• CAS: 341013-98-7
• 化学式: C₃₀H₄₉N₃O₁₀
• 分子量: 611.733
• InChiKey: MLRCOQWIYUROJS-XBELOMOVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  43
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  170
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  [(2R,3S,4R,5S,6R)-5-acetamido-3,4-diacetyloxy-6-[(2S)-3-[(2S,5R,6S,9R)-4,9-dimethyl-3-oxo-6-propan-2-yl-1,4-diazaspiro[4.5]decan-2-yl]-2-hydroxypropyl]oxan-2-yl]methyl acetate 在 盐酸 、 lithium hydroxide 作用下， 反应 2.0h， 生成 (2S,4S)-2-Amino-5-((2R,3S,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yl)-4-hydroxy-pentanoic acid
  参考文献：
  名称：

  Chiral Auxiliary Based Approach Toward the Synthesis of C-Glycosylated Amino Acids

  摘要：

  [GRAPHICS]In a chiral auxiliary based method C-glycosylated amino acids can be obtained by a 1,3-dipolar cycloaddition of a chiral glycine equivalent and C-1 allyl- or vinyl-derived carbohydrate building blocks as the key step. The products are formed regio- and diastereoselectively. Reductive cleavage of the N-O bond of the isoxazolidine and of the chiral auxiliary leads to C-glycosylated amino acids. The use of (-)-menthone to (+)-menthone as the auxiliary leads to the corresponding diastereomers.

  DOI：

  10.1021/ol015743j
• 作为产物：
  描述：

  [(2R,3S,4R,5S,6R)-5-acetamido-3,4-diacetyloxy-6-[[(2S,2'S,3aS,5'R,6S)-5,5'-dimethyl-4-oxo-2'-propan-2-ylspiro[3,3a-dihydro-2H-imidazo[1,5-b][1,2]oxazole-6,1'-cyclohexane]-2-yl]methyl]oxan-2-yl]methyl acetate 在 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以81%的产率得到[(2R,3S,4R,5S,6R)-5-acetamido-3,4-diacetyloxy-6-[(2S)-3-[(2S,5R,6S,9R)-4,9-dimethyl-3-oxo-6-propan-2-yl-1,4-diazaspiro[4.5]decan-2-yl]-2-hydroxypropyl]oxan-2-yl]methyl acetate
  参考文献：
  名称：

  Chiral Auxiliary Based Approach Toward the Synthesis of C-Glycosylated Amino Acids

  摘要：

  [GRAPHICS]In a chiral auxiliary based method C-glycosylated amino acids can be obtained by a 1,3-dipolar cycloaddition of a chiral glycine equivalent and C-1 allyl- or vinyl-derived carbohydrate building blocks as the key step. The products are formed regio- and diastereoselectively. Reductive cleavage of the N-O bond of the isoxazolidine and of the chiral auxiliary leads to C-glycosylated amino acids. The use of (-)-menthone to (+)-menthone as the auxiliary leads to the corresponding diastereomers.

  DOI：

  10.1021/ol015743j