2-(1',2'-O-isopropylidene-1',2'-dihydroxy-3',4'-diacetoxybutyl)-3-hydroxy-N-(9-phenylfluoren-9-yl)pyrrolidine | 133575-22-1

• 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'-dihydroxy-3',4'-diacetoxybutyl)-3-hydroxy-N-(9-phenylfluoren-9-yl)pyrrolidine
• CAS: 133575-22-1
• 化学式: C₃₄H₃₇NO₇
• 分子量: 571.67
• InChiKey: WYTCDSMVQHRWNW-PCYHVKPNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.41
• 重原子数：
  42.0
• 可旋转键数：
  7.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  94.53
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  2-(1',2'-O-isopropylidene-1',2'-dihydroxy-3',4'-diacetoxybutyl)-3-hydroxy-N-(9-phenylfluoren-9-yl)pyrrolidine 在 palladium on activated charcoal N-甲基咪唑 、 氢气 、 sodium acetate 、 potassium carbonate 、 三氟乙酸 、 三氟甲烷磺酸甲酯 作用下， 以 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 1.67h， 生成 栗精胺
  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：

  2-(1',2'-O-isopropylidene-1',2',3'-trihydroxy-4'-acetoxybutyl)-3-oxo-N-(9-phenylfluoren-9-yl)pyrrolidine 在 吡啶 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 四丁基醋酸铵 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 4.16h， 生成 2-(1',2'-O-isopropylidene-1',2'-dihydroxy-3',4'-diacetoxybutyl)-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