(3S,5R,6S,9R)-3-[(S)-2-Hydroxy-3-((2R,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-propyl]-6-isopropyl-1,9-dimethyl-1,4-diaza-spiro[4.5]decan-2-one | 341013-92-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3S,5R,6S,9R)-3-[(S)-2-Hydroxy-3-((2R,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-propyl]-6-isopropyl-1,9-dimethyl-1,4-diaza-spiro[4.5]decan-2-one
• CAS: 341013-92-1
• 化学式: C₅₀H₆₄N₂O₇
• 分子量: 805.067
• InChiKey: OHILHSNZSORRQE-BAZKDDSASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.09
• 重原子数：
  59.0
• 可旋转键数：
  18.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  98.72
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (3S,5R,6S,9R)-3-[(S)-2-Hydroxy-3-((2R,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-propyl]-6-isopropyl-1,9-dimethyl-1,4-diaza-spiro[4.5]decan-2-one 在 盐酸 、 lithium hydroxide 作用下， 反应 2.0h， 生成 (2S,4S)-2-Amino-4-hydroxy-5-((2R,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-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：

  (1S,2S,2'S,3a'S,5R)-2-isopropyl-5,5'-dimethyl-2'-(((2R,3S,4R,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)methyl)dihydro-2'H-spiro[cyclohexane-1,6'-imidazo[1,5-b]isoxazol]-4'(5'H)-one 在 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以79%的产率得到(3S,5R,6S,9R)-3-[(S)-2-Hydroxy-3-((2R,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-propyl]-6-isopropyl-1,9-dimethyl-1,4-diaza-spiro[4.5]decan-2-one
  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