3,5-dinitro-2-pyridyl-2,3,4-tri-O-benzyl-α-L-rhamnopyranose | 103383-31-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,5-dinitro-2-pyridyl-2,3,4-tri-O-benzyl-α-L-rhamnopyranose
• CAS: 103383-31-9
• 化学式: C₃₂H₃₁N₃O₉
• 分子量: 601.613
• InChiKey: DMLHYYKTPCEPHD-ITKKGFBLSA-N

物化性质

• 沸点：
  718.7±60.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.78
• 重原子数：
  44.0
• 可旋转键数：
  13.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  145.32
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  3,5-dinitro-2-pyridyl-2,3,4-tri-O-benzyl-α-L-rhamnopyranose 在 palladium on activated charcoal 4 A molecular sieve 、 三氟化硼乙醚 、 氢气 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， -40.0~25.0 ℃ 、101.33 kPa 条件下， 反应 1.33h， 生成 伊夫单甙
  参考文献：
  名称：

  Cardiac glycosides. 7. Sugar stereochemistry and cardiac glycoside activity

  摘要：

  Digitoxigenin alpha-L-, beta-L-, alpha-D-, and beta-D-glucosides; alpha-L-, beta-L-, alpha-D-, and beta-D-mannosides; and alpha-L- and beta-L-rhamnosides were stereoselectively synthesized from the corresponding sugar tetrabenzyl trichloroacetimidates. The Na+,K+-ATPase receptor inhibitory activities of these glycosides (as a measure of receptor binding) were compared with those of digitoxigenin, digitoxigenin 6'-hydroxy-beta-D-digitoxoside, digitoxigenin beta-D-galactoside, and digitoxigenin beta-D-digitoxoside. The observed activities reveal that a given sugar substituent may have a role in binding of some glycoside stereoisomers, but not others. With alpha-L- and possibly beta-L-rhamnosides, the 5'-CH3 and 4'-OH appear to have a predominant role in binding to the Na+,K+-ATPase receptor. Addition of a 6'-OH to form the corresponding mannosides dramatically disrupts the effect of both the 5'-CH3 and 4'-OH in prompting receptor binding of the alpha-L isomer. However, with the beta-L isomer, some influence of 4'-OH, 3'-OH, and 2'-OH binding remains. With beta-D-glycosides, binding via the "5'-CH3 site" appears to be of little importance and addition of a 6'-OH diminishes activity only slightly. With these beta-D-glycosides, an equatorial 4'-OH, axial 3'-OH, and equatorial 2'-OH groups appear to contribute to binding.

  DOI：

  10.1021/jm00160a025
• 作为产物：
  描述：

  甲基-Alpha-D-吡喃鼠李糖苷 在 2,6-二甲基吡啶 、 盐酸 、 potassium fluoride 、 氢氧化钾 、 18-冠醚-6 、 溶剂黄146 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.5h， 生成 3,5-dinitro-2-pyridyl-2,3,4-tri-O-benzyl-α-L-rhamnopyranose
  参考文献：
  名称：

  Cardiac glycosides. 7. Sugar stereochemistry and cardiac glycoside activity

  摘要：

  Digitoxigenin alpha-L-, beta-L-, alpha-D-, and beta-D-glucosides; alpha-L-, beta-L-, alpha-D-, and beta-D-mannosides; and alpha-L- and beta-L-rhamnosides were stereoselectively synthesized from the corresponding sugar tetrabenzyl trichloroacetimidates. The Na+,K+-ATPase receptor inhibitory activities of these glycosides (as a measure of receptor binding) were compared with those of digitoxigenin, digitoxigenin 6'-hydroxy-beta-D-digitoxoside, digitoxigenin beta-D-galactoside, and digitoxigenin beta-D-digitoxoside. The observed activities reveal that a given sugar substituent may have a role in binding of some glycoside stereoisomers, but not others. With alpha-L- and possibly beta-L-rhamnosides, the 5'-CH3 and 4'-OH appear to have a predominant role in binding to the Na+,K+-ATPase receptor. Addition of a 6'-OH to form the corresponding mannosides dramatically disrupts the effect of both the 5'-CH3 and 4'-OH in prompting receptor binding of the alpha-L isomer. However, with the beta-L isomer, some influence of 4'-OH, 3'-OH, and 2'-OH binding remains. With beta-D-glycosides, binding via the "5'-CH3 site" appears to be of little importance and addition of a 6'-OH diminishes activity only slightly. With these beta-D-glycosides, an equatorial 4'-OH, axial 3'-OH, and equatorial 2'-OH groups appear to contribute to binding.

  DOI：

  10.1021/jm00160a025