N'-methyl-N-(3,4,6-tri-O-benzyl-2-deoxy-2-nitro-β-D-glucopyranosyl)piperazine | 1352458-22-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N'-methyl-N-(3,4,6-tri-O-benzyl-2-deoxy-2-nitro-β-D-glucopyranosyl)piperazine
• 英文别名: 1-methyl-4-[(2R,3R,4R,5S,6R)-3-nitro-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]piperazine
• CAS: 1352458-22-0
• 化学式: C₃₂H₃₉N₃O₆
• 分子量: 561.678
• InChiKey: JDIOEXPFULGQDH-NYDDOVQGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  41
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  89.2
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  N-甲基哌嗪 、 3,4,6-tri-O-benzyl-2-nitro-D-glucal 以 二氯甲烷 为溶剂， 反应 24.0h， 以93%的产率得到N'-methyl-N-(3,4,6-tri-O-benzyl-2-deoxy-2-nitro-β-D-glucopyranosyl)piperazine
  参考文献：
  名称：

  Stereoselective synthesis of β-N-glycosides through 2-deoxy-2-nitroglycal

  摘要：

  An efficient, base-free protocol has been developed for the beta-stereoselective synthesis of N-glycosides from 2-nitroglycal and secondary amines. Simple protection and deprotection manipulations on the N-glycosides pave a way for the synthesis of biologically significant 1,2-diaminosugars and glycopeptides. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.01.032

文献信息

• Stereoselective synthesis of β-N-glycosides through 2-deoxy-2-nitroglycal
  作者：Shaohua Xiang、Jimei Ma、Bala Kishan Gorityala、Xue-Wei Liu

  DOI：10.1016/j.carres.2011.01.032

  日期：2011.12

  An efficient, base-free protocol has been developed for the beta-stereoselective synthesis of N-glycosides from 2-nitroglycal and secondary amines. Simple protection and deprotection manipulations on the N-glycosides pave a way for the synthesis of biologically significant 1,2-diaminosugars and glycopeptides. (C) 2011 Elsevier Ltd. All rights reserved.