methyl (2S,3S)-3-(methoxymethoxy)-4-oxo-1-(9-phenyl-9H-fluoren-9-yl)pyrrolidine-2-carboxylate | 206994-52-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: methyl (2S,3S)-3-(methoxymethoxy)-4-oxo-1-(9-phenyl-9H-fluoren-9-yl)pyrrolidine-2-carboxylate
• 英文别名: methyl (2S,3S)-3-(methoxymethoxy)-4-oxo-1-(9-phenylfluoren-9-yl)pyrrolidine-2-carboxylate
• CAS: 206994-52-7
• 化学式: C₂₇H₂₅NO₅
• 分子量: 443.499
• InChiKey: DNLOUWBZQSIROJ-LOSJGSFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (2S,3S)-3-(methoxymethoxy)-4-oxo-1-(9-phenyl-9H-fluoren-9-yl)pyrrolidine-2-carboxylate 在 二氯二茂锆 、 三乙基硼氢化锂 、 sodium carbonate 、 间氯过氧苯甲酸 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 33.0h， 生成 (2S,3S,4S)-4-Hydroxy-3-methoxymethoxy-4-methyl-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
• 作为产物：
  描述：

  氯甲基甲基醚 、 (2S,3S)-3-hydroxy-4-oxo-N-(9'-phenylfluoren-9'-yl)pyrrolidine-2-carboxylic acid methyl ester 在 N,N-二甲基苯胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以80%的产率得到methyl (2S,3S)-3-(methoxymethoxy)-4-oxo-1-(9-phenyl-9H-fluoren-9-yl)pyrrolidine-2-carboxylate
  参考文献：
  名称：

  Total Synthesis of Depsilairdin

  摘要：

  The total synthesis of depsilairdin, a host-selective phytotoxin isolated from Leptosphaeria maculans (the causal agent of blackleg disease of oilseed Brassicas), has been achieved by N-terminal extension of a suitably protected derivative of the hitherto unknown amino acid (2S,3S,4R)-3,4-dihydroxy-3-methyl-proline (Dhmp) followed by esterification with lairdinol A. The latter esterification, complicated by the sterically hindered nature of the carboxyl group, was accomplished by a novel method involving reaction of the 1-hydroxybenzotriazole (HOBt) derived active ester with the bromomagnesium alkoxide of lairdinol A. Three depsilairdin analogues were also prepared by replacing the Dhmp residue with L-proline and cis- and trans-4-hydroxy-L-proline. Phytotoxicity assays showed that the analogues were nontoxic to both blackleg-susceptible (brown mustard) and -resistant (canola) plants, suggesting that the presence of the Dhmp residue in depsilairdin is important for its host-selective toxicity toward brown mustard.

  DOI：

  10.1021/jo1009239