(7S,8R)-7,8-dihydroxy-6-(hydroxymethyl)-3,4a,6,7,8,8a-hexahydrothiopyrano[3,2-d]pyrimidin-4-one | 1202387-75-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃吡啶类
• 英文名称: (7S,8R)-7,8-dihydroxy-6-(hydroxymethyl)-3,4a,6,7,8,8a-hexahydrothiopyrano[3,2-d]pyrimidin-4-one
• CAS: 1202387-75-4
• 化学式: C₈H₁₂N₂O₄S
• 分子量: 232.26
• InChiKey: NARLASFPEUGMNO-OPLJAJGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  127
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-methyl-2-phenyl-1,3-oxathiolan-5-one 、 D-木糖 、 甲脒 在 Montmorillonite K-10 clay 作用下， 反应 0.15h， 以87%的产率得到(7S,8R)-7,8-dihydroxy-6-(hydroxymethyl)-3,4a,6,7,8,8a-hexahydrothiopyrano[3,2-d]pyrimidin-4-one
  参考文献：
  名称：

  A novel multicomponent synthesis of polyfunctionalized bicyclic tetrahydropyrimidinone derivatives via mercaptoacetylative ring transformations

  摘要：

  A novel K-10 clay (nanoclay)-catalyzed expeditious synthesis of polyfunctionalized bicyclic pyrimidines using unprotected aldoses, 2-methyl-2-phenyl-1,3-oxathiolan-5-one and amidines/guanidine is reported. These polyfunctionalized bicyclic pyrimidines were obtained in excellent yields (72-93%) with high cis diastereoselectivity (>94%) at the ring junction via tandem condensation, mercaptoacetylative ring transformation and cyclization reactions. The process presents an excellent illustration of use of carbohydrates as renewable resources for the formation of pharmaceutically relevant fine chemicals employing solvent-free microwave irradiation conditions in a one-pot procedure. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.06.017

文献信息

• A novel multicomponent synthesis of polyfunctionalized bicyclic tetrahydropyrimidinone derivatives via mercaptoacetylative ring transformations
  作者：Lal Dhar S. Yadav、Ankita Rai

  DOI：10.1016/j.carres.2009.06.017

  日期：2009.11

  A novel K-10 clay (nanoclay)-catalyzed expeditious synthesis of polyfunctionalized bicyclic pyrimidines using unprotected aldoses, 2-methyl-2-phenyl-1,3-oxathiolan-5-one and amidines/guanidine is reported. These polyfunctionalized bicyclic pyrimidines were obtained in excellent yields (72-93%) with high cis diastereoselectivity (>94%) at the ring junction via tandem condensation, mercaptoacetylative ring transformation and cyclization reactions. The process presents an excellent illustration of use of carbohydrates as renewable resources for the formation of pharmaceutically relevant fine chemicals employing solvent-free microwave irradiation conditions in a one-pot procedure. (C) 2009 Elsevier Ltd. All rights reserved.