(2S,4S,5R)-4-<(2-acetamido-4-O-benzoyl-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)oxy>-5-<(benzyloxy)methyl>-1,2-pyrrolidinedicarboxylic acid 2-methyl 1-(phenylmethyl) diester | 132592-37-1

• 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-4-O-benzoyl-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)oxy>-5-<(benzyloxy)methyl>-1,2-pyrrolidinedicarboxylic acid 2-methyl 1-(phenylmethyl) diester
• 英文别名: (2S,4S,5R)-4-[(2-acetamido-4-O-benzoyl-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)oxy]-5-[(benzyloxy)methyl]-1,2-pyrrolidinedicarboxylic acid 2-methyl 1-(phenylmethyl) diester
• CAS: 132592-37-1
• 化学式: C₅₁H₅₄N₂O₁₂
• 分子量: 886.996
• InChiKey: SHCNREYIMNCYLK-SRPKWCLYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  65.0
• 可旋转键数：
  19.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  157.39
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  (2S,4S,5R)-4-<(2-acetamido-4-O-benzoyl-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)oxy>-5-<(benzyloxy)methyl>-1,2-pyrrolidinedicarboxylic acid 2-methyl 1-(phenylmethyl) diester 在 氢氧化钾 、 氰基磷酸二乙酯 、 三氧化硫吡啶 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 98.0h， 生成 N-<(2S,4S,5R)-4-<(2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-sulfo-β-D-glucopyranosyl)oxy>-5-(hydroxymethyl)-L-prolyl>-6-aminopenicillinic acid bis(phenylmethyl ester)
  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
• 作为产物：
  描述：

  (5R,4S,2S)-4-acetoxy-5-<(E)-1-<2-(methoxycarbonyl)ethenyl>>-1,2-pyrrolidinedicarboxylic acid 2-methyl 1-(phenylmethyl) diester 在 sodium tetrahydroborate 、 4 A molecular sieve 、 sodium methylate 、 臭氧 、 silver(l) oxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 52.58h， 生成 (2S,4S,5R)-4-<(2-acetamido-4-O-benzoyl-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)oxy>-5-<(benzyloxy)methyl>-1,2-pyrrolidinedicarboxylic acid 2-methyl 1-(phenylmethyl) diester
  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