(2S,3R,4S)-4-Hydroxymethyl-3-methoxymethoxy-1-(9-phenyl-9H-fluoren-9-yl)-pyrrolidine-2-carboxylic acid methyl ester | 206994-57-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (2S,3R,4S)-4-Hydroxymethyl-3-methoxymethoxy-1-(9-phenyl-9H-fluoren-9-yl)-pyrrolidine-2-carboxylic acid methyl ester
• 英文别名: methyl (2S,3R,4S)-4-(hydroxymethyl)-3-(methoxymethoxy)-1-(9-phenylfluoren-9-yl)pyrrolidine-2-carboxylate
• CAS: 206994-57-2
• 化学式: C₂₈H₂₉NO₅
• 分子量: 459.542
• InChiKey: KHLBZFBPJVAROX-RRWZXMNXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  68.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,3R,4S)-4-Hydroxymethyl-3-methoxymethoxy-1-(9-phenyl-9H-fluoren-9-yl)-pyrrolidine-2-carboxylic acid methyl ester 在 palladium on activated charcoal 锂硼氢 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以97%的产率得到[(2R,3R,4S)-4-Hydroxymethyl-3-methoxymethoxy-1-(9-phenyl-9H-fluoren-9-yl)-pyrrolidin-2-yl]-methanol
  参考文献：
  名称：

  C-3- and C-4-Alkylated Polyhydroxypyrrolidines:  Enantiospecific Syntheses and Glycosidase Inhibitory Activity

  摘要：

  Short, efficient, and stereoselective syntheses of enantiomerically pure C-3- and C-4-alkylated analogues of (2R,3S,4R)-3,4-dihydroxy-2-(hydroxymethyl) a potent alpha-galactosidase inhibitor, from 4-hydroxy-L-proline are presented. Grignard addition or enolate alkylation of a N-(9-phenylfluoren-9-yl)-4-oxo-3-[(methoxymethyl)oxy]proline and epoxidation or hydroboration of a 4-methylene-3-[(methoxymethyl)oxy]proline proceeded with complete stereoselection and in excellent yields. The inhibitory activities of the synthesized pyrrolidines were measured and showed that the fit of A. niger alpha-galactosidase and the jack bean alpha-mannosidase around C-3 of the pyrrolidine ring (alpha face) must be very tight, while the fit around C-4 (alpha face) is much looser. Positioning a methylene group between the hydroxyl at C-4 and the pyrrolidine ring completely abolishes the inhibitory activity (see analogue 5).

  DOI：

  10.1021/jo980078m
• 作为产物：
  描述：

  methyl (2S,3S)-3-(methoxymethoxy)-4-oxo-1-(9-phenyl-9H-fluoren-9-yl)pyrrolidine-2-carboxylate 在 sodium hydroxide 、 二氯二茂锆 、 dimethyl sulfide borane 、 双氧水 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 7.0h， 生成 (2S,3R,4S)-4-Hydroxymethyl-3-methoxymethoxy-1-(9-phenyl-9H-fluoren-9-yl)-pyrrolidine-2-carboxylic acid methyl ester
  参考文献：
  名称：

  C-3- and C-4-Alkylated Polyhydroxypyrrolidines:  Enantiospecific Syntheses and Glycosidase Inhibitory Activity

  摘要：

  Short, efficient, and stereoselective syntheses of enantiomerically pure C-3- and C-4-alkylated analogues of (2R,3S,4R)-3,4-dihydroxy-2-(hydroxymethyl) a potent alpha-galactosidase inhibitor, from 4-hydroxy-L-proline are presented. Grignard addition or enolate alkylation of a N-(9-phenylfluoren-9-yl)-4-oxo-3-[(methoxymethyl)oxy]proline and epoxidation or hydroboration of a 4-methylene-3-[(methoxymethyl)oxy]proline proceeded with complete stereoselection and in excellent yields. The inhibitory activities of the synthesized pyrrolidines were measured and showed that the fit of A. niger alpha-galactosidase and the jack bean alpha-mannosidase around C-3 of the pyrrolidine ring (alpha face) must be very tight, while the fit around C-4 (alpha face) is much looser. Positioning a methylene group between the hydroxyl at C-4 and the pyrrolidine ring completely abolishes the inhibitory activity (see analogue 5).

  DOI：

  10.1021/jo980078m

文献信息

• C-3- and C-4-Alkylated Polyhydroxypyrrolidines:  Enantiospecific Syntheses and Glycosidase Inhibitory Activity
  作者：María-Jesús Blanco、F. Javier Sardina

  DOI：10.1021/jo980078m

  日期：1998.5.1

  Short, efficient, and stereoselective syntheses of enantiomerically pure C-3- and C-4-alkylated analogues of (2R,3S,4R)-3,4-dihydroxy-2-(hydroxymethyl) a potent alpha-galactosidase inhibitor, from 4-hydroxy-L-proline are presented. Grignard addition or enolate alkylation of a N-(9-phenylfluoren-9-yl)-4-oxo-3-[(methoxymethyl)oxy]proline and epoxidation or hydroboration of a 4-methylene-3-[(methoxymethyl)oxy]proline proceeded with complete stereoselection and in excellent yields. The inhibitory activities of the synthesized pyrrolidines were measured and showed that the fit of A. niger alpha-galactosidase and the jack bean alpha-mannosidase around C-3 of the pyrrolidine ring (alpha face) must be very tight, while the fit around C-4 (alpha face) is much looser. Positioning a methylene group between the hydroxyl at C-4 and the pyrrolidine ring completely abolishes the inhibitory activity (see analogue 5).