5-{(2SR,3S,4R)-1-[(9H-fluoren-9-ylmethoxy)carbonyl]-3,4-dihydroxypyrrolidin-2-yl}-2-methylfuran-3-carboxylic acid | 484687-12-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 5-{(2SR,3S,4R)-1-[(9H-fluoren-9-ylmethoxy)carbonyl]-3,4-dihydroxypyrrolidin-2-yl}-2-methylfuran-3-carboxylic acid
• CAS: 484687-12-9
• 化学式: C₂₅H₂₃NO₇
• 分子量: 449.46
• InChiKey: LSRHQPJWYZOWKP-WPLVIQRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.31
• 重原子数：
  33.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  120.44
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  5-{(2SR,3S,4R)-1-[(9H-fluoren-9-ylmethoxy)carbonyl]-3,4-dihydroxypyrrolidin-2-yl}-2-methylfuran-3-carboxylic acid 在 吡啶 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (2S,3S,4R)-3,4-Diacetoxy-2-(4-isopropylcarbamoyl-5-methyl-furan-2-yl)-pyrrolidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester
  参考文献：
  名称：

  Synthesis of [(2S,3S,4R)-3,4-Dihydroxypyrrolidin-2-yl]-5-methylfuran-4-carboxylic Acid Derivatives: New Leads as Selective β-Galactosidase Inhibitors

  摘要：

  The preparation of [(2S,3S,4R)-3,4-dihydroxypyrrolidin-2-yl]furan derivatives in a stereoselective route starting from D-glucose and ethyl acetoacetate is presented. Ethyl ester (6), N,N-diethylamide (7) and N-isopropylamide (8) have been tested towards 25 glycosidases. Ester (6) is a selective inhibitor of beta-galactosidases. The new compounds represent a new type of imino-C-nucleoside analogues. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(02)00397-9
• 作为产物：
  描述：

  (3S,4R)-2-(4-Carboxy-5-methyl-furan-2-yl)-3,4-bis-trimethylsilanyloxy-pyrrolidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester 在 水 作用下， 生成 5-{(2SR,3S,4R)-1-[(9H-fluoren-9-ylmethoxy)carbonyl]-3,4-dihydroxypyrrolidin-2-yl}-2-methylfuran-3-carboxylic acid
  参考文献：
  名称：

  Synthesis of [(2S,3S,4R)-3,4-Dihydroxypyrrolidin-2-yl]-5-methylfuran-4-carboxylic Acid Derivatives: New Leads as Selective β-Galactosidase Inhibitors

  摘要：

  The preparation of [(2S,3S,4R)-3,4-dihydroxypyrrolidin-2-yl]furan derivatives in a stereoselective route starting from D-glucose and ethyl acetoacetate is presented. Ethyl ester (6), N,N-diethylamide (7) and N-isopropylamide (8) have been tested towards 25 glycosidases. Ester (6) is a selective inhibitor of beta-galactosidases. The new compounds represent a new type of imino-C-nucleoside analogues. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(02)00397-9

文献信息

• Synthesis and Glycosidase Inhibitory Activities of 5-(1′,4′-Dideoxy-1′,4′-imino-D-erythrosyl)-2-methyl-3-furoic Acid (=5-[(3S,4R)-3,4-Dihydroxypyrrolidin-2-yl]-2-methylfuran-3-carboxylic Acid) Derivatives: New Leads as Selective -L-Fucosidase and -Galactosidase Inhibitors
  作者：Antonio J. Moreno-Vargas、Inmaculada Robina、Raynald Demange、Pierre Vogel

  DOI：10.1002/hlca.200390152

  日期：2003.6

  The García-González reaction of D-glucose and ethyl acetoacetate generated ethyl 5-[(1′S)-D-erythrosyl]-2-methyl-3-furoate (5), which was converted to ethyl 5-[(1′R)-1′,4′-dideoxy-1′,4′-imino-D-erythrosyl]-2-methyl-3-furoate (3c) and to ethyl 5-[(1′S)-1′,4′-dideoxy-1′,4′-imino-D-erythrosyl]-2-methyl-3-furoate (4c). Similar methods were developed to generate other carboxylic acid derivatives such as

  D-葡萄糖与乙酰乙酸乙酯的García-González反应生成5-[（1 'S）-D-赤藓糖基] -2-甲基-3-糠酸乙酯（5），然后将其转化为5-[（1' R）-1'，4'-二脱氧-1'，4'-亚氨基-D-赤藓基] -2-甲基-3-糠酸酯（3c）和乙基5-[（1 'S）-1'，4 ′-二脱氧-1′，4′-亚氨基-D-赤藓糖基] -2-甲基-3-糠酸酯（4c）。开发了类似的方法来生成其他羧酸衍生物，例如甲基（参见3e和4e），异丙基（参见3f）和丁酯（参见3g），S-苯基（参见3a）和S-乙基硫酯（请参见3m），N-苄基甲酰胺3b和4b，甘氨酸衍生的酰胺3h和N-苯基（请参见3i），N-异丙基（请参见3j和4j），N，N-二乙基-（请参见3k和4k）和N-乙基羧酰胺（参见3l）。所有新的5-（1'，4'-dideoxy-1'，4'-亚氨基-D-赤藓糖基）-3-糠酸（= 5-[（3 S，4