2-<(9-phenylfluoren-9-yl)amino>-2-deoxy-3,4:5,6-di-O-isopropylidene-D-mannose | 133473-13-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 2-<(9-phenylfluoren-9-yl)amino>-2-deoxy-3,4:5,6-di-O-isopropylidene-D-mannose
• 英文别名: 2-[(9-phenylfluoren-9-yl)-amino]-2-deoxy-3,4;5,6-di-O-isopropylidene-D-mannose；(2S)-2-[(4R,5S)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]-2-[(9-phenylfluoren-9-yl)amino]acetaldehyde
• CAS: 133473-13-9
• 化学式: C₃₁H₃₃NO₅
• 分子量: 499.607
• InChiKey: YWWLPOVAIPOOFT-BIYDSLDMSA-N

物化性质

• 沸点：
  598.1±50.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  37
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-<(9-phenylfluoren-9-yl)amino>-2-deoxy-3,4:5,6-di-O-isopropylidene-D-mannose 在 palladium dihydroxide 、 palladium on activated charcoal 咪唑 、 indium 、 Dowex 50W-X₈ 、 水 、 氢气 、 sodium acetate 、 potassium carbonate 、 臭氧 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 58.58h， 生成 (1S,6R,7R,8R,8aR)-1,2,3,5,6,7,8,8a-八氢吲嗪-1,6,7,8-四醇
  参考文献：
  名称：

  Simple Total Syntheses of (+)-Castanospermine and (+)-6-Epicastanospermine Using Indium-Mediated Allylation

  摘要：

  铟介导的α-氨基醛3从D-葡萄糖-δ-内酯的亲核烯丙基化反应提供了优异的二元立体选择性合成的顺式氨基醇。顺式氨基醇很容易应用于强效糖苷酶抑制剂的总合成；（+）-卡斯塔诺斯珀明和（+）-6-去乙酰卡斯塔诺斯珀明。

  DOI：

  10.1055/s-2003-42423
• 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 、 二异丁基氢化铝 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 54.33h， 生成 2-<(9-phenylfluoren-9-yl)amino>-2-deoxy-3,4:5,6-di-O-isopropylidene-D-mannose
  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

• Simple Total Syntheses of (+)-Castanospermine and (+)-6-Epicastanospermine Using Indium-Mediated Allylation
  作者：Ki Hun Park、Jin Hyo Kim、Woo Duck Seo、Jin Hwan Lee、Byong Won Lee

  DOI：10.1055/s-2003-42423

  日期：——

  The indium-mediated allylation of α-aminoaldehyde 3 from d-glucono-δ-lactone provided the syn-aminoalcohol with excellent diastereoselectivity. syn-Aminoalcohol was easily applied to the total syntheses of the potent glycosidase inhibitors; (+)-castanospermine and (+)-6-epicastanospermine.

  铟介导的α-氨基醛3从D-葡萄糖-δ-内酯的亲核烯丙基化反应提供了优异的二元立体选择性合成的顺式氨基醇。顺式氨基醇很容易应用于强效糖苷酶抑制剂的总合成；（+）-卡斯塔诺斯珀明和（+）-6-去乙酰卡斯塔诺斯珀明。
• 2-Amino-2-deoxyhexoses as chiral educts for hydroxylated indolizidines. Synthesis of (+)-castanospermine and (+)-6-epicastanospermine
  作者：Marc Gerspacher、Henry Rapoport

  DOI：10.1021/jo00011a047

  日期：1991.5

  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.