2-(1',2'-O-isopropylidene-1',2',3',4'-tetrahydroxybutyl)-3-oxo-N-(9-phenylfluoren-9-yl)pyrrolidine | 133473-17-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 2-(1',2'-O-isopropylidene-1',2',3',4'-tetrahydroxybutyl)-3-oxo-N-(9-phenylfluoren-9-yl)pyrrolidine
• 英文别名: (2S)-2-[(4R,5R)-5-[(1R)-1,2-dihydroxyethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(9-phenylfluoren-9-yl)pyrrolidin-3-one
• CAS: 133473-17-3
• 化学式: C₃₀H₃₁NO₅
• 分子量: 485.58
• InChiKey: JHSXKDMWEDXCON-BIYDSLDMSA-N

物化性质

• 熔点：
  >150 °C
• 沸点：
  641.1±55.0 °C(predicted)
• 密度：
  1.297±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.48
• 重原子数：
  36.0
• 可旋转键数：
  5.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  79.23
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-(1',2'-O-isopropylidene-1',2',3',4'-tetrahydroxybutyl)-3-oxo-N-(9-phenylfluoren-9-yl)pyrrolidine 在 N-甲基咪唑 、 sodium tetrahydroborate 、 三氟甲烷磺酸甲酯 作用下， 以 乙醇 为溶剂， 反应 8.17h， 生成 2-(1',2'-O-isopropylidene-4'-O-tosyl-1',2',3',4'-tetrahydroxybutyl)-3-hydroxy-N-(9-phenylfluoren-9-yl)pyrrolidine
  参考文献：
  名称：

  2-Amino-2-deoxyhexoses as chiral educts for hydroxylated indolizidines. Synthesis of (+)-castanospermine and (+)-6-epicastanospermine

  摘要：

  D-2-Amino-2-deoxyglucosaminic acid, obtained from D-glucosamine, and a D-2-amino-2-deoxymannosaminic acid derivative, obtained from D-glucono-delta-lactone, were derivatized and converted to the corresponding configurationally stable aldehydes. The N-(9-phenylfuoren-9-yl)-protected mannosamine derivative was readily transformed into a variety of configurationally stable alpha-amino ketones, thus providing convenient and versatile chiral educts. These educts may be envisaged as derivable from polyhydroxy alpha-amino acids. Examples of the utility of these chiral educts are provided by the efficient conversion of a D-mannosaminic acid derivative into the polyhydroxy indolizidine alkaloids (+)-castanospermine and (+)-6-epicastanospermine.

  DOI：

  10.1021/jo00011a047
• 作为产物：
  描述：

  9-溴-9-苯基芴 在 N-氯代丁二酰亚胺 、 lead(II) nitrate 、 二甲基硫 、 水 、 氢溴酸 、 二异丁基氢化铝 、 碳酸氢钠 、 sodium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 64.17h， 生成 2-(1',2'-O-isopropylidene-1',2',3',4'-tetrahydroxybutyl)-3-oxo-N-(9-phenylfluoren-9-yl)pyrrolidine
  参考文献：
  名称：

  2-Amino-2-deoxyhexoses as chiral educts for hydroxylated indolizidines. Synthesis of (+)-castanospermine and (+)-6-epicastanospermine

  摘要：

  D-2-Amino-2-deoxyglucosaminic acid, obtained from D-glucosamine, and a D-2-amino-2-deoxymannosaminic acid derivative, obtained from D-glucono-delta-lactone, were derivatized and converted to the corresponding configurationally stable aldehydes. The N-(9-phenylfuoren-9-yl)-protected mannosamine derivative was readily transformed into a variety of configurationally stable alpha-amino ketones, thus providing convenient and versatile chiral educts. These educts may be envisaged as derivable from polyhydroxy alpha-amino acids. Examples of the utility of these chiral educts are provided by the efficient conversion of a D-mannosaminic acid derivative into the polyhydroxy indolizidine alkaloids (+)-castanospermine and (+)-6-epicastanospermine.

  DOI：

  10.1021/jo00011a047

文献信息

• GERSPACHER, MARC;RAPOPORT, HENRY, J. ORG. CHEM., 56,(1991) N1, C. 3700-3706
  作者：GERSPACHER, MARC、RAPOPORT, HENRY

  DOI：——

  日期：——