(3R,4R,5R)-methyl 3-(benzyloxycarbonylamino)-4-(tert-butoxycarbonylamino)-5-hydroxycyclopent-1-enecarboxylate | 1180656-13-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3R,4R,5R)-methyl 3-(benzyloxycarbonylamino)-4-(tert-butoxycarbonylamino)-5-hydroxycyclopent-1-enecarboxylate
• 英文别名: methyl (3R,4R,5R)-5-hydroxy-4-[(2-methylpropan-2-yl)oxycarbonylamino]-3-(phenylmethoxycarbonylamino)cyclopentene-1-carboxylate
• CAS: 1180656-13-6
• 化学式: C₂₀H₂₆N₂O₇
• 分子量: 406.436
• InChiKey: DTZPUMWMDAGZSB-BZUAXINKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  123
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (3R,4R,5R)-methyl 3-(benzyloxycarbonylamino)-4-(tert-butoxycarbonylamino)-5-hydroxycyclopent-1-enecarboxylate 、 乙酰氯 在 盐酸 、 甲醇 、 sodium carbonate 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 以70%的产率得到(3R,4R,5R)-methyl 4-acetamido-3-(benzyloxycarbonylamino)-5-hydroxy-cyclopent-1-enecarboxylate
  参考文献：
  名称：

  Development of New Stereodiverse Diaminocyclitols as Inhibitors of Influenza Virus Neuraminidase

  摘要：

  A concise and modular approach to synthesize a new type of cyclopentene-based diaminocyclitol library from D-serine and L-serine has been developed, and key steps in this synthesis are an aza-Claisen rearrangement, a ring-closing metathesis, and a Baylis-Hillman reaction. The developed chemistry may offer a unique way to Investigate the neuraminidase (NA) mutation by systematically mapping the changes within its binding sites.

  DOI：

  10.1021/ol902438f
• 作为产物：
  描述：

  (3S,4R,5R)-methyl 5-(benzyloxycarbonylamino)-4-(tert-butoxy-carbonylamino)-3-hydroxy-2-methylenehept-6-enoate 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以77%的产率得到(3R,4R,5R)-methyl 3-(benzyloxycarbonylamino)-4-(tert-butoxycarbonylamino)-5-hydroxycyclopent-1-enecarboxylate
  参考文献：
  名称：

  Development of New Stereodiverse Diaminocyclitols as Inhibitors of Influenza Virus Neuraminidase

  摘要：

  A concise and modular approach to synthesize a new type of cyclopentene-based diaminocyclitol library from D-serine and L-serine has been developed, and key steps in this synthesis are an aza-Claisen rearrangement, a ring-closing metathesis, and a Baylis-Hillman reaction. The developed chemistry may offer a unique way to Investigate the neuraminidase (NA) mutation by systematically mapping the changes within its binding sites.

  DOI：

  10.1021/ol902438f