ethyl [(1R,2R,3S,4R,5S)-5,6-dideoxy-1,2-O-isopropylidene-3-O-methyl-5-(N¹-heptyl-N³-benzyl-1-ureidyl)-1,4-heptofuranos-5-yl]uronoate | 623559-46-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl [(1R,2R,3S,4R,5S)-5,6-dideoxy-1,2-O-isopropylidene-3-O-methyl-5-(N¹-heptyl-N³-benzyl-1-ureidyl)-1,4-heptofuranos-5-yl]uronoate
• CAS: 623559-46-6
• 化学式: C₂₈H₄₄N₂O₇
• 分子量: 520.667
• InChiKey: NNISZCBKRHTXSI-BKCLZSIZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.38
• 重原子数：
  37.0
• 可旋转键数：
  14.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  95.56
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  ethyl [(1R,2R,3S,4R,5S)-5,6-dideoxy-1,2-O-isopropylidene-3-O-methyl-5-(N¹-heptyl-N³-benzyl-1-ureidyl)-1,4-heptofuranos-5-yl]uronoate 在 4 A molecular sieve 、 四丁基溴化铵 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲苯 为溶剂， 反应 2.5h， 以85%的产率得到(1'R,2'R,3'S,4'R,6S)-N¹-heptyl-N³-benzyl-5,6-dihydro-(1',2'-O-isopropylidene-3'-O-methyl-1',2',3',4'-tetrahydrofuranos-4'-yl)pyrimidin-2,4-dione
  参考文献：
  名称：

  Synthesis and bioevaluation of glycosyl ureas as α-glucosidase inhibitors and their effect on mycobacterium

  摘要：

  Glycosyl amino esters (2-13) on reaction with different isocyanates resulted in quantitative conversion to glycosyl ureas (14-32). Few of the selected ureas (15-20, 22-28, 30 and 32) on cyclative amidation with DBU/TBAB/4 Angstrom MS gave respective dihydropyrimidinones in fair to good yields (33-47). The compounds were screened for alpha-glucosidase inhibitory activity and two (19 and 23) of them showed strong inhibition against rat intestinal (x-glucosidase. The compounds were also screened against Mycobacterium aurum, however, only one (19) of them exhibited marginal antitubercular activity. (C) 2000 Elsevier Science Ltd. All rights reserved. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00214-1
• 作为产物：
  描述：

  庚胺 以 乙醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 ethyl [(1R,2R,3S,4R,5S)-5,6-dideoxy-1,2-O-isopropylidene-3-O-methyl-5-(N¹-heptyl-N³-benzyl-1-ureidyl)-1,4-heptofuranos-5-yl]uronoate
  参考文献：
  名称：

  Synthesis and bioevaluation of glycosyl ureas as α-glucosidase inhibitors and their effect on mycobacterium

  摘要：

  Glycosyl amino esters (2-13) on reaction with different isocyanates resulted in quantitative conversion to glycosyl ureas (14-32). Few of the selected ureas (15-20, 22-28, 30 and 32) on cyclative amidation with DBU/TBAB/4 Angstrom MS gave respective dihydropyrimidinones in fair to good yields (33-47). The compounds were screened for alpha-glucosidase inhibitory activity and two (19 and 23) of them showed strong inhibition against rat intestinal (x-glucosidase. The compounds were also screened against Mycobacterium aurum, however, only one (19) of them exhibited marginal antitubercular activity. (C) 2000 Elsevier Science Ltd. All rights reserved. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00214-1