5-Azido-5-deoxy-2,3-O-isopropylidene-D-ribose-dimethylacetal | 162895-61-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-Azido-5-deoxy-2,3-O-isopropylidene-D-ribose-dimethylacetal
• 英文别名: (1R)-2-azido-1-[(4R,5R)-5-(dimethoxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]ethanol
• CAS: 162895-61-6
• 化学式: C₁₀H₁₉N₃O₅
• 分子量: 261.278
• InChiKey: JWIOBJOHMRPRPF-BWZBUEFSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  71.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-Azido-5-deoxy-2,3-O-isopropylidene-D-ribose-dimethylacetal 在 盐酸 、 氨 、 sodium 、 三乙胺 、 三苯基膦 、 红铝 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 164.0h， 生成 (2S,3S,4R,5S)-3,4-dihydroxy-5-methylpyrrolidine-2-carbonitrile
  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：

  2,3-O-isopropylidene-5-O-p-tolylsulfonyl-D-ribose dimethyl acetal 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 以86%的产率得到5-Azido-5-deoxy-2,3-O-isopropylidene-D-ribose-dimethylacetal
  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.