O-[(4R,5R,6S)-6-acetamido-4,5-diacetoxy-3-acetoxymethylcyclohex-2-enylidene]amino N-phenylcarbamate | 1091630-29-3

• 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: O-[(4R,5R,6S)-6-acetamido-4,5-diacetoxy-3-acetoxymethylcyclohex-2-enylidene]amino N-phenylcarbamate
• CAS: 1091630-29-3
• 化学式: C₂₂H₂₅N₃O₉
• 分子量: 475.455
• InChiKey: MCYLSDCOXWSGRA-MSOLHYBRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.46
• 重原子数：
  34.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  158.69
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  O-[(4R,5R,6S)-6-acetamido-4,5-diacetoxy-3-acetoxymethylcyclohex-2-enylidene]amino N-phenylcarbamate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以95%的产率得到O-[(4R,5R,6S)-6-acetamido-4,5-dihydroxy-3-hydroxymethylcyclohex-2-enylidene]amino N-phenylcarbamate
  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：

  O-[(4R,5R,6S)-6-acetamido-4,5-dibenzyloxy-3-benzyloxymethylcyclohex-2-enylidene]amino N-phenylcarbamate 、 乙酸酐 在 iron(III) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以48%的产率得到O-[(4R,5R,6S)-6-acetamido-4,5-diacetoxy-3-acetoxymethylcyclohex-2-enylidene]amino N-phenylcarbamate
  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