benzhydryl (3R,4S,5S,6S)-6-acetamido-4-((Z)-2,3-bis(tert-butoxycarbonyl)guanidino)-1-(2-ethylbutanoyl)-5-hydroxypiperidine-3-carboxylate | 876313-91-6

• 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: benzhydryl (3R,4S,5S,6S)-6-acetamido-4-((Z)-2,3-bis(tert-butoxycarbonyl)guanidino)-1-(2-ethylbutanoyl)-5-hydroxypiperidine-3-carboxylate
• CAS: 876313-91-6
• 化学式: C₃₈H₅₃N₅O₉
• 分子量: 723.867
• InChiKey: LWNSQPIDMZYHGE-NYTDTBNFSA-N

物化性质

• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.81
• 重原子数：
  52.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  184.96
• 氢给体数：
  4.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  benzhydryl (3R,4S,5S,6S)-6-acetamido-4-((Z)-2,3-bis(tert-butoxycarbonyl)guanidino)-1-(2-ethylbutanoyl)-5-hydroxypiperidine-3-carboxylate 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 12.0h， 以90%的产率得到(3R,4S,5S,6S)-6-Acetylamino-1-(2-ethyl-butyryl)-4-guanidino-5-hydroxy-piperidine-3-carboxylic acid
  参考文献：
  名称：

  Synthesis and biological evaluation of gem-diamine 1-N-iminosugars related to l-iduronic acid as inhibitors of heparan sulfate 2-O-sulfotransferase

  摘要：

  A variety of gem-diamine 1-N-iminosugars related to L-iduronic acid were synthesized and evaluated as inhibitors of heparan sulfate uronyl 2-O-sulfotransferase using an in vitro enzyme assay. Two iminosugars containing guanidino groups acted as potent inhibitors of the enzyme. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.10.055
• 作为产物：
  描述：

  (3aS,4S,7R,7aS)-4-Acetylamino-5-(2-ethyl-butyryl)-2-trichloromethyl-3a,4,5,6,7,7a-hexahydro-oxazolo[5,4-c]pyridine-7-carboxylic acid benzhydryl ester 在 吡啶 、 sodium tetrahydroborate 、 对甲苯磺酸 、 三乙胺 、 mercury dichloride 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 benzhydryl (3R,4S,5S,6S)-6-acetamido-4-((Z)-2,3-bis(tert-butoxycarbonyl)guanidino)-1-(2-ethylbutanoyl)-5-hydroxypiperidine-3-carboxylate
  参考文献：
  名称：

  Synthesis and biological evaluation of gem-diamine 1-N-iminosugars related to l-iduronic acid as inhibitors of heparan sulfate 2-O-sulfotransferase

  摘要：

  A variety of gem-diamine 1-N-iminosugars related to L-iduronic acid were synthesized and evaluated as inhibitors of heparan sulfate uronyl 2-O-sulfotransferase using an in vitro enzyme assay. Two iminosugars containing guanidino groups acted as potent inhibitors of the enzyme. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.10.055