(S)-N-((1S,2R,3R,4R,5R)-2-Benzyloxymethyl-3,4,5-trihydroxy-cyclopentyl)-2-hydroxy-2-phenyl-acetamide | 207516-62-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-N-((1S,2R,3R,4R,5R)-2-Benzyloxymethyl-3,4,5-trihydroxy-cyclopentyl)-2-hydroxy-2-phenyl-acetamide
• 英文别名: (2S)-2-hydroxy-2-phenyl-N-[(1S,2R,3R,4R,5R)-2,3,4-trihydroxy-5-(phenylmethoxymethyl)cyclopentyl]acetamide
• CAS: 207516-62-9
• 化学式: C₂₁H₂₅NO₆
• 分子量: 387.433
• InChiKey: OVAPLCYTLSIXSA-IPJCAIGPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  119
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (S)-N-((1S,2R,3R,4R,5R)-2-Benzyloxymethyl-3,4,5-trihydroxy-cyclopentyl)-2-hydroxy-2-phenyl-acetamide 在 4-二甲氨基吡啶 作用下， 以 吡啶 为溶剂， 以90%的产率得到Acetic acid (1R,2R,3R,4R,5S)-2,3-diacetoxy-4-benzyloxymethyl-5-((S)-2-hydroxy-2-phenyl-acetylamino)-cyclopentyl ester
  参考文献：
  名称：

  Enantioselective Approaches to Aminocyclopentitols:  A Total Synthesis of (+)-6-Epitrehazolin and a Formal Total Synthesis of (+)-Trehazolin

  摘要：

  Potent inhibitors of trehalase, such as trehazolin and its congeners, represent an attractive approach to the design of effective new insect control agents. In this report, enantioselective total syntheses of (-)-6-epitrehazolin and (+)-trehazolin were achieved using the asymmetric heterocycloaddition between [(benzyloxy)methyl]cyclopentadiene and the acylnitroso compound arising from in situ oxidation of (S)-mandelohydroxamic acid with tetrabutylammonium periodate. Further function- alization of the resulting 3,4,5-trisubstituted cyclopentene, either involving osmylation or epoxidation of the double bond, efficiently created pentasubstituted cyclopentanes. Introduction of the quaternary carbon in both synthesis targets was achieved via stereoselective osmylation of an intermediate 2,3,4,5-substituted 1-methylenecyclopentane.

  DOI：

  10.1021/jo980050a
• 作为产物：
  描述：

  (S)-N-((1R,4S,5R)-5-Benzyloxymethyl-4-hydroxy-cyclopent-2-enyl)-2-hydroxy-2-phenyl-acetamide 在 三氟过氧乙酸 、 间氯过氧苯甲酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 52.0h， 生成 (S)-N-((1S,2R,3R,4R,5R)-2-Benzyloxymethyl-3,4,5-trihydroxy-cyclopentyl)-2-hydroxy-2-phenyl-acetamide
  参考文献：
  名称：

  Enantioselective Approaches to Aminocyclopentitols:  A Total Synthesis of (+)-6-Epitrehazolin and a Formal Total Synthesis of (+)-Trehazolin

  摘要：

  Potent inhibitors of trehalase, such as trehazolin and its congeners, represent an attractive approach to the design of effective new insect control agents. In this report, enantioselective total syntheses of (-)-6-epitrehazolin and (+)-trehazolin were achieved using the asymmetric heterocycloaddition between [(benzyloxy)methyl]cyclopentadiene and the acylnitroso compound arising from in situ oxidation of (S)-mandelohydroxamic acid with tetrabutylammonium periodate. Further function- alization of the resulting 3,4,5-trisubstituted cyclopentene, either involving osmylation or epoxidation of the double bond, efficiently created pentasubstituted cyclopentanes. Introduction of the quaternary carbon in both synthesis targets was achieved via stereoselective osmylation of an intermediate 2,3,4,5-substituted 1-methylenecyclopentane.

  DOI：

  10.1021/jo980050a