(2S,4S,5R)-5-((benzyloxy)methyl)-4-hydroxy-1,2-pyrrolidinedicarboxylic acid bis-(phenylmethyl ester) | 129001-55-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S,4S,5R)-5-((benzyloxy)methyl)-4-hydroxy-1,2-pyrrolidinedicarboxylic acid bis-(phenylmethyl ester)
• 英文别名: dibenzyl (2S,4S,5R)-4-hydroxy-5-(phenylmethoxymethyl)pyrrolidine-1,2-dicarboxylate
• CAS: 129001-55-4
• 化学式: C₂₈H₂₉NO₆
• 分子量: 475.541
• InChiKey: PUOYIBPMRYDRNO-NXCFDTQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  85.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  O-(2-azido-4-O-benzoyl-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl) trichloroacetimidate 、 (2S,4S,5R)-5-((benzyloxy)methyl)-4-hydroxy-1,2-pyrrolidinedicarboxylic acid bis-(phenylmethyl ester) 在 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 以10%的产率得到(2S,4S,5R)-4-<(2-azido-4-O-benzoyl-3,6-di-O-benzyl-2-deoxy-α-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
• 作为产物：
  描述：

  (5R,4S,2S)-4-acetoxy-5-((phenylmethoxy)methyl)-1,2-pyrrolidinedicarboxylic acid 2-methyl 1-(phenylmethyl) diester 、 苯甲醇 在 titanium(IV) isopropylate 作用下， 反应 9.0h， 以82%的产率得到(2S,4S,5R)-5-((benzyloxy)methyl)-4-hydroxy-1,2-pyrrolidinedicarboxylic 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

文献信息

• BARRETT, ANTHONY G. M.;PILIPAUSKAS, DANIEL, J. ORG. CHEM., 55,(1990) N8, C. 5194-5196
  作者：BARRETT, ANTHONY G. M.、PILIPAUSKAS, DANIEL

  DOI：——

  日期：——