2-(1',2'-O-isopropylidene-4'-O-tosyl-1',2',3',4'-tetrahydroxybutyl)-3-hydroxy-N-(9-phenylfluoren-9-yl)pyrrolidine | 133473-19-5

• 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-4'-O-tosyl-1',2',3',4'-tetrahydroxybutyl)-3-hydroxy-N-(9-phenylfluoren-9-yl)pyrrolidine
• 英文别名: [(2R)-2-hydroxy-2-[(4R,5R)-5-[(2R,3S)-3-hydroxy-1-(9-phenylfluoren-9-yl)pyrrolidin-2-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]ethyl] 4-methylbenzenesulfonate
• CAS: 133473-19-5
• 化学式: C₃₇H₃₉NO₇S
• 分子量: 641.785
• InChiKey: OHDQEDIVTGYAGI-IVSKGHNCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.99
• 重原子数：
  46.0
• 可旋转键数：
  8.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  105.53
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  2-(1',2'-O-isopropylidene-4'-O-tosyl-1',2',3',4'-tetrahydroxybutyl)-3-hydroxy-N-(9-phenylfluoren-9-yl)pyrrolidine 在 palladium on activated charcoal 氢气 、 sodium acetate 作用下， 以 甲醇 为溶剂， 以92%的产率得到1,6,7,8-tetrahydroxy-7,8-O-isopropylideneindolizidine
  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-甲基咪唑 、 sodium tetrahydroborate 、 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 、 三氟甲烷磺酸甲酯 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 72.33h， 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

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：——