N-[(1R,2R,3S,4R)-2,3-dibenzyloxy-4-benzyloxymethyl-4-hydroxy-6-oxocyclohexyl]acetamide | 1091630-21-5

• 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: N-[(1R,2R,3S,4R)-2,3-dibenzyloxy-4-benzyloxymethyl-4-hydroxy-6-oxocyclohexyl]acetamide
• CAS: 1091630-21-5
• 化学式: C₃₀H₃₃NO₆
• 分子量: 503.595
• InChiKey: NSNULTXRMIZQSV-RRGQHJHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.58
• 重原子数：
  37.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  94.09
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  N-[(1R,2R,3S,4R)-2,3-dibenzyloxy-4-benzyloxymethyl-4-hydroxy-6-oxocyclohexyl]acetamide 在 吡啶 、 磺酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以69%的产率得到N-[(1R,5R,6R)-5,6-dibenzyloxy-4-benzyloxymethyl-2-oxocyclohex-3-enyl]acetamide
  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：

  N-[(1S,2R,3S,4R,6S)-2,3-benzyloxy-4-benzyloxymethyl-4,6-dihydroxycyclohexyl]acetamide 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以90%的产率得到N-[(1R,2R,3S,4R)-2,3-dibenzyloxy-4-benzyloxymethyl-4-hydroxy-6-oxocyclohexyl]acetamide
  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