(E)-{ethyl [(4'R,5'R,6'S)-6'-acetamido-4',5'-diacetoxy-3'-acetoxymethylcyclohex-2'-enylidene]acetate} | 1091630-32-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (E)-{ethyl [(4'R,5'R,6'S)-6'-acetamido-4',5'-diacetoxy-3'-acetoxymethylcyclohex-2'-enylidene]acetate}
• CAS: 1091630-32-8
• 化学式: C₁₉H₂₅NO₉
• 分子量: 411.409
• InChiKey: NATSFUQKEULPEL-IHJBRZCVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.35
• 重原子数：
  29.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  134.3
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (E)-{ethyl [(4'R,5'R,6'S)-6'-acetamido-4',5'-diacetoxy-3'-acetoxymethylcyclohex-2'-enylidene]acetate} 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以79%的产率得到(E)-{ethyl 2-[(4'R,5'R,6'S)-6'-acetamido-4',5'-dihydroxy-3'-hydroxymethylcyclohex-2'-enylidene]acetate}
  参考文献：
  名称：

  The synthesis and biological evaluation of some carbocyclic analogues of PUGNAc

  摘要：

  The synthesis of some analogues of O-(2-acetamido-2-deoxy-D-glucopyranosylidene)amino N-phenylcarbamate, PUGNAc, an inhibitor of beta-N-acetylglucosaminidases, is described. The analogues were tested against a range of beta-N-acetylglucosaminidases to establish any biological activity. As well, the analogues were tested as inhibitors of a uridine diphosphate-N-acetyl-D-glucosamine: polypeptidyl transferase, OGT, a critical protein involved in the post-translational modification of nuclear and cytosolic proteins by N-acetyl-D-glucosamine. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.08.012
• 作为产物：
  描述：

  (E)-{ethyl [(4'R,5'R,6'S)-6'-acetamido-4',5'-dibenzyloxy-3'-benzyloxymethylcyclohex-2'-enylidene]acetate} 、 乙酸酐 在 iron(III) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以81%的产率得到(E)-{ethyl [(4'R,5'R,6'S)-6'-acetamido-4',5'-diacetoxy-3'-acetoxymethylcyclohex-2'-enylidene]acetate}
  参考文献：
  名称：

  The synthesis and biological evaluation of some carbocyclic analogues of PUGNAc

  摘要：

  The synthesis of some analogues of O-(2-acetamido-2-deoxy-D-glucopyranosylidene)amino N-phenylcarbamate, PUGNAc, an inhibitor of beta-N-acetylglucosaminidases, is described. The analogues were tested against a range of beta-N-acetylglucosaminidases to establish any biological activity. As well, the analogues were tested as inhibitors of a uridine diphosphate-N-acetyl-D-glucosamine: polypeptidyl transferase, OGT, a critical protein involved in the post-translational modification of nuclear and cytosolic proteins by N-acetyl-D-glucosamine. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.08.012