methyl 2-<(9-phenylfluoren-9-yl)amino>-2-deoxy-3,4:5,6-di-O-isopropylidene-D-gluconate | 133473-14-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: methyl 2-<(9-phenylfluoren-9-yl)amino>-2-deoxy-3,4:5,6-di-O-isopropylidene-D-gluconate
• 英文别名: methyl 2-[(9-phenylfluoren-9-yl)amino]-2-deoxy-3,4:5,6-di-O-isopropylidene-D-gluconate
• CAS: 133473-14-0
• 化学式: C₃₂H₃₅NO₆
• 分子量: 529.633
• InChiKey: HBNREHLHHJAYTM-BIYDSLDMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.76
• 重原子数：
  39.0
• 可旋转键数：
  6.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  75.25
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  methyl 2-<(9-phenylfluoren-9-yl)amino>-2-deoxy-3,4:5,6-di-O-isopropylidene-D-gluconate 在 N-氯代丁二酰亚胺 、 二甲基硫 、 二异丁基氢化铝 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 6.33h， 生成 2-<(9-phenylfluoren-9-yl)amino>-2-deoxy-3,4:5,6-di-O-isopropylidene-D-glucose
  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：

  D-氨基葡萄糖酸 、 9-溴-9-苯基芴 、 2,2-二甲氧基丙烷 生成 methyl 2-<(9-phenylfluoren-9-yl)amino>-2-deoxy-3,4:5,6-di-O-isopropylidene-D-gluconate
  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