(2S,4S,5R)-4-<(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)oxy>-5-<(benzyloxy)methyl>-1,2-pyrrolidinedicarboxylic acid bis(phenylmethyl ester) | 129001-57-6

• 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-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)oxy>-5-<(benzyloxy)methyl>-1,2-pyrrolidinedicarboxylic acid bis(phenylmethyl ester)
• 英文别名: (2S,4S,5R)-4-[(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)oxy]-5-[(benzyloxy)methyl]-1,2-pyrrolidinedicarboxylic acid bis(phenylmethyl ester)
• CAS: 129001-57-6
• 化学式: C₅₀H₅₄N₂O₁₁
• 分子量: 858.986
• InChiKey: ITWAORYCFHKHNC-SVJHCJOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  63.0
• 可旋转键数：
  19.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  151.32
• 氢给体数：
  2.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  (2S,4S,5R)-4-<(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)oxy>-5-<(benzyloxy)methyl>-1,2-pyrrolidinedicarboxylic acid bis(phenylmethyl ester) 在 三氧化硫吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以65%的产率得到(2S,4S,5R)-4-<(2-acetamido-4-O-sulfo-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)oxy>-5-<(benzyloxy)methyl>-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
• 作为产物：
  描述：

  tert-Butyldimethylsilyl-2-azido-2-desoxy-4,6-O-isopropyliden-β-D-glucopyranosid 在 4-二甲氨基吡啶 、 氢氧化钾 、 4 A molecular sieve 、 四丁基氟化铵 、 四丁基溴化铵 、 四丁基碘化铵 、 sodium hydride 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 三氟乙酸 、 三丁基氧化锡 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 73.0h， 生成 (2S,4S,5R)-4-<(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)oxy>-5-<(benzyloxy)methyl>-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

• Total syntheses of bulgecinine and bulgecin C from (2S,4R)-hydroxyproline
  作者：Anthony G. M. Barrett、Daniel Pilipauskas

  DOI：10.1021/jo00305a007

  日期：1990.8