(2R,3R,4R,5R)-3,4-Diacetoxy-2-acetoxymethyl-5-(4-methoxy-phenyl)-pyrrolidine-1-carboxylic acid methyl ester | 534573-29-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (2R,3R,4R,5R)-3,4-Diacetoxy-2-acetoxymethyl-5-(4-methoxy-phenyl)-pyrrolidine-1-carboxylic acid methyl ester
• 英文别名: methyl (2R,3R,4R,5R)-3,4-diacetyloxy-2-(acetyloxymethyl)-5-(4-methoxyphenyl)pyrrolidine-1-carboxylate
• CAS: 534573-29-0
• 化学式: C₂₀H₂₅NO₉
• 分子量: 423.42
• InChiKey: PMXADMPZWPDPKP-NCXUSEDFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  118
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,5R)-3,4-Diacetoxy-2-acetoxymethyl-5-(4-methoxy-phenyl)-pyrrolidine-1-carboxylic acid methyl ester 在 ruthenium trichloride sodium periodate 作用下， 以 水 、 乙酸乙酯 、 乙腈 为溶剂， 反应 3.0h， 以67%的产率得到(2S,3R,4R,5R)-3,4-Diacetoxy-5-acetoxymethyl-pyrrolidine-1,2-dicarboxylic acid 1-methyl ester
  参考文献：
  名称：

  Synthesis of dihydroxylated prolines and iminocyclitols from five-membered endocyclic enecarbamates. Total synthesis of the potent glycosidase inhibitor (2R,3R,4R,5R)-2,5-dihydroxymethyl-3,4-dihydroxypyrrolidine (DMDP)

  摘要：

  cis- and trans-3,4-Dihydroxylated prolines and the iminocyclitol 1,4-dideoxy-1,4-imino ribitol were synthesized employing a strategy involving the Heck arylation of five-membered endocyclic enecarbarnates with aryldiazonium salts followed by oxidative cleavage of the electron-rich aromatic ring. The total synthesis of the potent alpha- and beta-glucosidase inhibitor (2R,3R,4R,5R)-2,5-hydroxymethyl-3,4-dihydroxypyrrolidine (DMDP) was also achieved by the same strategy in ten steps from a chiral five-membered enecarbamate in 12% overall yield. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00017-0
• 作为产物：
  描述：

  (1R,2S,4S,5S)-2-Hydroxymethyl-4-(4-methoxy-phenyl)-6-oxa-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid methyl ester 在 4-二甲氨基吡啶 、 硫酸 、 水 作用下， 以 1,4-二氧六环 、 吡啶 、 二氯甲烷 为溶剂， 反应 4.5h， 生成 (2R,3R,4R,5R)-3,4-Diacetoxy-2-acetoxymethyl-5-(4-methoxy-phenyl)-pyrrolidine-1-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis of dihydroxylated prolines and iminocyclitols from five-membered endocyclic enecarbamates. Total synthesis of the potent glycosidase inhibitor (2R,3R,4R,5R)-2,5-dihydroxymethyl-3,4-dihydroxypyrrolidine (DMDP)

  摘要：

  cis- and trans-3,4-Dihydroxylated prolines and the iminocyclitol 1,4-dideoxy-1,4-imino ribitol were synthesized employing a strategy involving the Heck arylation of five-membered endocyclic enecarbarnates with aryldiazonium salts followed by oxidative cleavage of the electron-rich aromatic ring. The total synthesis of the potent alpha- and beta-glucosidase inhibitor (2R,3R,4R,5R)-2,5-hydroxymethyl-3,4-dihydroxypyrrolidine (DMDP) was also achieved by the same strategy in ten steps from a chiral five-membered enecarbamate in 12% overall yield. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00017-0