(2S,2'S,3aS,5'R,6S)-5,5'-dimethyl-2'-propan-2-yl-2-[[(2S,3S,4R,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]methyl]spiro[3,3a-dihydro-2H-imidazo[1,5-b][1,2]oxazole-6,1'-cyclohexane]-4-one | 341013-65-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,2'S,3aS,5'R,6S)-5,5'-dimethyl-2'-propan-2-yl-2-[[(2S,3S,4R,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]methyl]spiro[3,3a-dihydro-2H-imidazo[1,5-b][1,2]oxazole-6,1'-cyclohexane]-4-one
• CAS: 341013-65-8
• 化学式: C₅₀H₆₂N₂O₇
• 分子量: 803.051
• InChiKey: KAZDCSQUJJHWDM-NVRROLLLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  59
• 可旋转键数：
  16
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2S,2'S,3aS,5'R,6S)-5,5'-dimethyl-2'-propan-2-yl-2-[[(2S,3S,4R,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]methyl]spiro[3,3a-dihydro-2H-imidazo[1,5-b][1,2]oxazole-6,1'-cyclohexane]-4-one 在 盐酸 、 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 (2S,4S)-2-Amino-4-hydroxy-5-((2S,3S,4R,5R,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：

  1-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranos-1-yl)-2-propene 、 (-)-menthone nitrone 以 甲苯 为溶剂， 反应 36.0h， 以92%的产率得到(2S,2'S,3aS,5'R,6S)-5,5'-dimethyl-2'-propan-2-yl-2-[[(2S,3S,4R,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]methyl]spiro[3,3a-dihydro-2H-imidazo[1,5-b][1,2]oxazole-6,1'-cyclohexane]-4-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

文献信息

• Chiral Auxiliary Based Approach Toward the Synthesis of C-Glycosylated Amino Acids
  作者：Bernhard Westermann、Armin Walter、Ulrich Flörke、Hans-Josef Altenbach

  DOI：10.1021/ol015743j

  日期：2001.5.1

  [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.