[1'-(5''-deoxyuridin)-1'H-1',2',3'-triazol-4'-yl] methyl 2-acetamido-2-deoxy-α-D-galactopyranoside | 1152423-07-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [1'-(5''-deoxyuridin)-1'H-1',2',3'-triazol-4'-yl] methyl 2-acetamido-2-deoxy-α-D-galactopyranoside
• 英文别名: N-[(2S,3R,4R,5R,6R)-2-[[1-[[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl]triazol-4-yl]methoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• CAS: 1152423-07-8
• 化学式: C₂₀H₂₈N₆O₁₁
• 分子量: 528.476
• InChiKey: NTNSUCAAOPXZHU-ODEXHHBCSA-N

物化性质

• 密度：
  1.90±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -5.2
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  238
• 氢给体数：
  7
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  prop-2-yn-1-yl 2-acetamido-2-deoxy-α-D-galactopyranoside 、 5'-azido-5'-deoxyuridine 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 水 、 叔丁醇 为溶剂， 反应 20.0h， 以97%的产率得到[1'-(5''-deoxyuridin)-1'H-1',2',3'-triazol-4'-yl] methyl 2-acetamido-2-deoxy-α-D-galactopyranoside
  参考文献：
  名称：

  Probing replacement of pyrophosphate via click chemistry; synthesis of UDP-sugar analogues as potential glycosyl transferase inhibitors

  摘要：

  A series of potential UDP-sugar mimics were readily synthesised by copper(I) catalysed modified Huisgen cycloaddition of the corresponding alpha-propargyl glycosides with 5-azido uridine in aqueous solution. None of the compounds accessed displayed significant inhibitory activity at concentrations of up to 4.5 mM in an assay against bovine milk beta-1,4-galactosyltransferase. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.01.001

文献信息

• Probing replacement of pyrophosphate via click chemistry; synthesis of UDP-sugar analogues as potential glycosyl transferase inhibitors
  作者：Kar Kheng Yeoh、Terry D. Butters、Brendan L. Wilkinson、Antony J. Fairbanks

  DOI：10.1016/j.carres.2009.01.001

  日期：2009.3

  A series of potential UDP-sugar mimics were readily synthesised by copper(I) catalysed modified Huisgen cycloaddition of the corresponding alpha-propargyl glycosides with 5-azido uridine in aqueous solution. None of the compounds accessed displayed significant inhibitory activity at concentrations of up to 4.5 mM in an assay against bovine milk beta-1,4-galactosyltransferase. (C) 2009 Elsevier Ltd. All rights reserved.