(2R,3R,4R,5R)-N-(β-D-glucopyranosyl)thiocarbamoyl-3,4-dihydroxy-2,5-di(hydroxymethyl)-pyrrolidine | 697288-31-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4R,5R)-N-(β-D-glucopyranosyl)thiocarbamoyl-3,4-dihydroxy-2,5-di(hydroxymethyl)-pyrrolidine
• 英文别名: (2R,3R,4R,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)-N-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]pyrrolidine-1-carbothioamide
• CAS: 697288-31-6
• 化学式: C₁₃H₂₄N₂O₉S
• 分子量: 384.408
• InChiKey: UXXUMYBOPJYUNQ-ZDLXXCOVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.6
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  218
• 氢给体数：
  9
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,5R)-N-(β-D-glucopyranosyl)thiocarbamoyl-3,4-dihydroxy-2,5-di(hydroxymethyl)-pyrrolidine 在 mercury(II) oxide 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以70%的产率得到(5R,6R,7R,8R)-1-aza-2-(β-D-glucopyranosyl)imino-6,7-dihydroxy-8-hydroxymethyl-3-oxabicyclo[3.3.0]octane
  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：

  (-)-3-deoxy-1,2:4,5-di-O-isopropylidene-β-D-fructofuranos-3-yl benzoate 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 53.5h， 生成 (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

文献信息

• Pseudoamide-Type Pyrrolidine and Pyrrolizidine Glycomimetics and Their Inhibitory Activities against Glycosidases
  作者：M. Isabel García-Moreno、David Rodríguez-Lucena、Carmen Ortiz Mellet、José M. García Fernández

  DOI：10.1021/jo0499221

  日期：2004.5.1

  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.