(2R,3R,4R,5R)-3,4-dihydroxy-2,5-di(hydroxymethyl)-N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thiocarbamoylpyrrolidine | 697288-30-5

• 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: (2R,3R,4R,5R)-3,4-dihydroxy-2,5-di(hydroxymethyl)-N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thiocarbamoylpyrrolidine
• CAS: 697288-30-5
• 化学式: C₂₁H₃₂N₂O₁₃S
• 分子量: 552.557
• InChiKey: FJFHYIWJCIGVFN-KQRZPSHASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.3
• 重原子数：
  37.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  210.62
• 氢给体数：
  5.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,5R)-3,4-dihydroxy-2,5-di(hydroxymethyl)-N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thiocarbamoylpyrrolidine 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以100%的产率得到(2R,3R,4R,5R)-N-(β-D-glucopyranosyl)thiocarbamoyl-3,4-dihydroxy-2,5-di(hydroxymethyl)-pyrrolidine
  参考文献：
  名称：

  Pseudoamide-Type Pyrrolidine and Pyrrolizidine Glycomimetics and Their Inhibitory Activities against Glycosidases

  摘要：

  Coupling reaction of (2R,3R,4R,5R)-2,5-hydroxymethyl-3,4-dihydroxypyrrolidine (DMDP) with isothiocyanates afforded the corresponding thiourea adducts, which were transformed into isourea-type bicyclic oxapyrrolizidine glycomimetics by mercury(II) oxide-assisted intramolecular sulfur displacement. Cyclic carbamate and thiocarbamate analogues were also prepared by direct carbonylation or thiocarbonylation of DMDP. Evaluation of the glycosidase inhibitory properties demonstrated that remarkable specificities in enzyme inhibition can be achieved upon modifications on the pseudoaglyconic side chain and on the nature of the sp(2)-hybridized endocyclic ring nitrogen.

  DOI：

  10.1021/jo0499221
• 作为产物：
  描述：

  1,2;4,5-di-O-isopropylidene-β-D-(-)-fructopyranose 在 palladium on activated charcoal 吡啶 、 咪唑 、 六甲基磷酰三胺 、 sodium azide 、 氢气 、 碘 、 sodium methylate 、 溶剂黄146 、 三苯基膦 、 三氟乙酸 作用下， 以 甲醇 、 水 、 甲苯 为溶剂， -65.0~80.0 ℃ 、400.0 kPa 条件下， 反应 56.5h， 生成 (2R,3R,4R,5R)-3,4-dihydroxy-2,5-di(hydroxymethyl)-N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thiocarbamoylpyrrolidine
  参考文献：
  名称：

  Pseudoamide-Type Pyrrolidine and Pyrrolizidine Glycomimetics and Their Inhibitory Activities against Glycosidases

  摘要：

  Coupling reaction of (2R,3R,4R,5R)-2,5-hydroxymethyl-3,4-dihydroxypyrrolidine (DMDP) with isothiocyanates afforded the corresponding thiourea adducts, which were transformed into isourea-type bicyclic oxapyrrolizidine glycomimetics by mercury(II) oxide-assisted intramolecular sulfur displacement. Cyclic carbamate and thiocarbamate analogues were also prepared by direct carbonylation or thiocarbonylation of DMDP. Evaluation of the glycosidase inhibitory properties demonstrated that remarkable specificities in enzyme inhibition can be achieved upon modifications on the pseudoaglyconic side chain and on the nature of the sp(2)-hybridized endocyclic ring nitrogen.

  DOI：

  10.1021/jo0499221