(3R,4S,5S,6S)-6-Acetylamino-1-(2-ethyl-butyryl)-5-hydroxy-4-(2,2,2-trichloro-acetylamino)-piperidine-3-carboxylic acid benzhydryl ester | 876313-89-2

• 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,4S,5S,6S)-6-Acetylamino-1-(2-ethyl-butyryl)-5-hydroxy-4-(2,2,2-trichloro-acetylamino)-piperidine-3-carboxylic acid benzhydryl ester
• CAS: 876313-89-2
• 化学式: C₂₉H₃₄Cl₃N₃O₆
• 分子量: 626.964
• InChiKey: DZCYDUITPQCZHZ-FVEXOFTDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.89
• 重原子数：
  41.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  125.04
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (3R,4S,5S,6S)-6-Acetylamino-1-(2-ethyl-butyryl)-5-hydroxy-4-(2,2,2-trichloro-acetylamino)-piperidine-3-carboxylic acid benzhydryl ester 在 盐酸 、 sodium tetrahydroborate 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 14.0h， 生成 (3R,4S,5S,6S)-6-Acetylamino-4-amino-1-(2-ethyl-butyryl)-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 、 对甲苯磺酸 作用下， 反应 2.0h， 以77%的产率得到(3R,4S,5S,6S)-6-Acetylamino-1-(2-ethyl-butyryl)-5-hydroxy-4-(2,2,2-trichloro-acetylamino)-piperidine-3-carboxylic acid benzhydryl ester
  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