N-[(E)-(1S,2R,3S,4R)-2,3-dibenzyloxy-4-benzyloxymethyl-4-hydroxy-6-(hydroxyimino)cyclohexyl]acetamide | 1091630-26-0

• 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-[(E)-(1S,2R,3S,4R)-2,3-dibenzyloxy-4-benzyloxymethyl-4-hydroxy-6-(hydroxyimino)cyclohexyl]acetamide
• CAS: 1091630-26-0
• 化学式: C₃₀H₃₄N₂O₆
• 分子量: 518.61
• InChiKey: PIKZTZQBHVOXHO-JAQBZQASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.84
• 重原子数：
  38.0
• 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：
  109.61
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  N-[(E)-(1S,2R,3S,4R)-2,3-dibenzyloxy-4-benzyloxymethyl-4-hydroxy-6-(hydroxyimino)cyclohexyl]acetamide 、 异氰酸苯酯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以69%的产率得到O-[(2S,3R,4S,5R)-2-acetamido-3,4-dibenzyloxy-5-benzyloxymethyl-5-hydroxycyclohexylidene]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：

  N-[(1R,2R,3S,4R)-2,3-dibenzyloxy-4-benzyloxymethyl-4-hydroxy-6-oxocyclohexyl]acetamide 在 盐酸羟胺 、 sodium acetate trihydrate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 以86%的产率得到N-[(E)-(1S,2R,3S,4R)-2,3-dibenzyloxy-4-benzyloxymethyl-4-hydroxy-6-(hydroxyimino)cyclohexyl]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