(2S,4S,5R)-4-<(2-acetamido-2-deoxy-β-D-glucopyranosyl)oxy>-5-(hydroxymethyl)-1,2-pyrrolidinedicarboxylic acid | 92953-57-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,4S,5R)-4-<(2-acetamido-2-deoxy-β-D-glucopyranosyl)oxy>-5-(hydroxymethyl)-1,2-pyrrolidinedicarboxylic acid
• 英文别名: (2S,4S,5R)-4-[(2-acetamido-2-deoxy-β-D-glucopyranosyl)oxy]-5-(hydroxymethyl)-1,2-pyrrolidinedicarboxylic acid；(2S,4S,5R)-4-[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5-(hydroxymethyl)pyrrolidine-2-carboxylic acid
• CAS: 92953-57-6
• 化学式: C₁₄H₂₄N₂O₉
• 分子量: 364.353
• InChiKey: HUHGHGSEWTYCLU-IZHHZIKYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.6
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  178
• 氢给体数：
  7
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  (2S,4S)-Methyl 4-acetoxy-1-<<2-(trimethylsilyl)ethyl>oxycarbonyl>pyrrolidine-2-carboxylate 在 钯 氢氧化钾 、 sodium tetrahydroborate 、 甲酸 、 4 A molecular sieve 、 硫酸 、 camphor-10-sulfonic acid 、 sodium methylate 、 六正丁基二锡 、 碳酸氢钠 、 臭氧 、 silver(l) oxide 作用下， 以 甲醇 、 二氯甲烷 、 溶剂黄146 、 异丙醇 、 苯 为溶剂， 反应 162.17h， 生成 (2S,4S,5R)-4-<(2-acetamido-2-deoxy-β-D-glucopyranosyl)oxy>-5-(hydroxymethyl)-1,2-pyrrolidinedicarboxylic acid
  参考文献：
  名称：

  Electrochemical oxidation of proline derivatives: total syntheses of bulgecinine and bulgecin C

  摘要：

  The influence of structure on the efficiency of the electrochemical C-5 oxidation of (2S,4S)-hydroxyproline carbamate esters is presented. Optimum methoxylation was observed with (2S,4S)-4-acetoxy-1,2-pyrrolidine-dicarboxylic acid 2-methyl 1-(2-(trimethylsily)ethyl) ester (19). The corresponding C-5 methoxy derivative 20 was converted into bulgecinine (4) via a stereospecific radical homologation to incorporate the C-5 hydroxymethyl substituent. Bulgecin C (1c) was prepared via a beta-stereoselective glycosidation reaction using a 2-azido-2-deoxy-alpha-D-glucopyranosyl trichloroacetimidate derivative, regiospecific C-4' sulfation, and deprotection.

  DOI：

  10.1021/jo00008a040

文献信息

• Structures of bulgecins, bacterial metabolites with bulge-inducing activity
  作者：Susumu Shinagawa、Fumiko Kasahara、Yoshikazu Wada、Setsuo Harada、Mitsuko Asai

  DOI：10.1016/s0040-4020(01)91497-8

  日期：1984.1
• Electrochemical oxidation of proline derivatives: total syntheses of bulgecinine and bulgecin C
  作者：Anthony G. M. Barrett、Daniel Pilipauskas

  DOI：10.1021/jo00008a040

  日期：1991.4

  The influence of structure on the efficiency of the electrochemical C-5 oxidation of (2S,4S)-hydroxyproline carbamate esters is presented. Optimum methoxylation was observed with (2S,4S)-4-acetoxy-1,2-pyrrolidine-dicarboxylic acid 2-methyl 1-(2-(trimethylsily)ethyl) ester (19). The corresponding C-5 methoxy derivative 20 was converted into bulgecinine (4) via a stereospecific radical homologation to incorporate the C-5 hydroxymethyl substituent. Bulgecin C (1c) was prepared via a beta-stereoselective glycosidation reaction using a 2-azido-2-deoxy-alpha-D-glucopyranosyl trichloroacetimidate derivative, regiospecific C-4' sulfation, and deprotection.