N-(Benzyloxycarbonyl)-5(R)-<(benzyloxy)methyl>-3(R),4(R)-bis(benzyloxy)-2(S)-(9-guaninylmethyl)pyrrolidine | 162895-77-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: N-(Benzyloxycarbonyl)-5(R)-<(benzyloxy)methyl>-3(R),4(R)-bis(benzyloxy)-2(S)-(9-guaninylmethyl)pyrrolidine
• 英文别名: benzyl (2S,3R,4R,5R)-2-[(2-amino-6-oxo-1H-purin-9-yl)methyl]-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)pyrrolidine-1-carboxylate
• CAS: 162895-77-4
• 化学式: C₄₀H₄₀N₆O₆
• 分子量: 700.794
• InChiKey: CZBJNHNBPTVJTB-BTHRSQNSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  52
• 可旋转键数：
  15
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  143
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N-(Benzyloxycarbonyl)-5(R)-<(benzyloxy)methyl>-3(R),4(R)-bis(benzyloxy)-2(S)-(9-guaninylmethyl)pyrrolidine 在 三氯化硼 作用下， 以 二氯甲烷 为溶剂， 以37.2%的产率得到5(R)-(Hydroxymethyl)-3(R),4(R)-dihydroxy-2(S)-(9-guaninylmethyl)pyrrolidine
  参考文献：
  名称：

  Synthesis and Evaluation of Homoaza Sugars as Glycosidase Inhibitors

  摘要：

  In an effort to develop transition-state mimetics of the glycosidase-catalyzed reaction, five- and six-membered azasugars and their home-analogs were prepared and tested as inhibitors of glycosidases. Inhibition studies indicate that the fucosyl cationlike, five-membered imine 1 and its reduced form 2 are potent inhibitors of alpha-fucosidase from bovine kidney with respective K-i values of 160 nM and 2 mu M. The five-membered homoaminoazasugar 3 is also a potent inhibitor of the enzyme (K-i = 1.9 x 10(-6) M), while the glucose and mannose-like six-membered homoaminoazasugars 4 and 5 are less potent than the corresponding 1-deoxyazasugars as inhibitors of alpha-glucosidase and alpha-mannosidase, respectively. The primary amino group was placed in an attempt to introduce additional electrostatic interactions in the active site. The inhibitory activities are, however, in the high mu M range. Synthesis of homoazasugars structurally related to a disaccharide and a nucleoside is also described.

  DOI：

  10.1021/jo00111a007
• 作为产物：
  描述：

  2,5-二(羟基甲基)-3,4-吡咯烷二醇 在 吡啶 、 氢氧化钾 、 sodium methylate 、 sodium hydride 、 碳酸氢钠 、 potassium carbonate 、 三乙胺 、 2-巯基乙醇 、 potassium iodide 作用下， 以 甲醇 、 二氯甲烷 、 乙二醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 83.0h， 生成 N-(Benzyloxycarbonyl)-5(R)-<(benzyloxy)methyl>-3(R),4(R)-bis(benzyloxy)-2(S)-(9-guaninylmethyl)pyrrolidine
  参考文献：
  名称：

  Synthesis and Evaluation of Homoaza Sugars as Glycosidase Inhibitors

  摘要：

  In an effort to develop transition-state mimetics of the glycosidase-catalyzed reaction, five- and six-membered azasugars and their home-analogs were prepared and tested as inhibitors of glycosidases. Inhibition studies indicate that the fucosyl cationlike, five-membered imine 1 and its reduced form 2 are potent inhibitors of alpha-fucosidase from bovine kidney with respective K-i values of 160 nM and 2 mu M. The five-membered homoaminoazasugar 3 is also a potent inhibitor of the enzyme (K-i = 1.9 x 10(-6) M), while the glucose and mannose-like six-membered homoaminoazasugars 4 and 5 are less potent than the corresponding 1-deoxyazasugars as inhibitors of alpha-glucosidase and alpha-mannosidase, respectively. The primary amino group was placed in an attempt to introduce additional electrostatic interactions in the active site. The inhibitory activities are, however, in the high mu M range. Synthesis of homoazasugars structurally related to a disaccharide and a nucleoside is also described.

  DOI：

  10.1021/jo00111a007

文献信息

• Synthesis and Evaluation of Homoaza Sugars as Glycosidase Inhibitors
  作者：Chi-Huey Wong、Louis Provencher、John A. Porco、Sang-Hun Jung、Yi-Fong Wang、Lihren Chen、Ruo Wang、Darryl H. Steensma

  DOI：10.1021/jo00111a007

  日期：1995.3

  In an effort to develop transition-state mimetics of the glycosidase-catalyzed reaction, five- and six-membered azasugars and their home-analogs were prepared and tested as inhibitors of glycosidases. Inhibition studies indicate that the fucosyl cationlike, five-membered imine 1 and its reduced form 2 are potent inhibitors of alpha-fucosidase from bovine kidney with respective K-i values of 160 nM and 2 mu M. The five-membered homoaminoazasugar 3 is also a potent inhibitor of the enzyme (K-i = 1.9 x 10(-6) M), while the glucose and mannose-like six-membered homoaminoazasugars 4 and 5 are less potent than the corresponding 1-deoxyazasugars as inhibitors of alpha-glucosidase and alpha-mannosidase, respectively. The primary amino group was placed in an attempt to introduce additional electrostatic interactions in the active site. The inhibitory activities are, however, in the high mu M range. Synthesis of homoazasugars structurally related to a disaccharide and a nucleoside is also described.