Acetic acid (1S,2S,3R,4R,5S)-3-acetoxy-2-bromo-4-hydroxymethyl-5-phenylacetylamino-cyclopentyl ester | 207516-43-6

• 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: Acetic acid (1S,2S,3R,4R,5S)-3-acetoxy-2-bromo-4-hydroxymethyl-5-phenylacetylamino-cyclopentyl ester
• 英文别名: [(1R,2S,3S,4S,5R)-3-acetyloxy-2-bromo-5-(hydroxymethyl)-4-[(2-phenylacetyl)amino]cyclopentyl] acetate
• CAS: 207516-43-6
• 化学式: C₁₈H₂₂BrNO₆
• 分子量: 428.28
• InChiKey: DKCMHCNRGRXITR-OGCZYDBJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Acetic acid (1S,2S,3R,4R,5S)-3-acetoxy-2-bromo-4-hydroxymethyl-5-phenylacetylamino-cyclopentyl ester 在 盐酸 、 4-二甲氨基吡啶 、 四氧化锇 、 2-硝基苯基丝氰酸酯 、 三丁基膦 、 双氧水 、 N-甲基吗啉氧化物 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 270.0h， 生成 1-((1R,2R,3R,4R,5S)-4-Bromo-2,3,5-trihydroxy-2-hydroxymethyl-cyclopentyl)-3-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-thiourea
  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 palladium dihydroxide 4-二甲氨基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 氢气 作用下， 以 1,4-二氧六环 、 乙醇 、 水 为溶剂， 反应 22.0h， 生成 Acetic acid (1S,2S,3R,4R,5S)-3-acetoxy-2-bromo-4-hydroxymethyl-5-phenylacetylamino-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