4-methylumbelliferyl 2-acetamido-2-deoxy-4,6-O-di-tert-butylsilanediyl-β-D-glucopyranoside | 1319721-54-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 4-methylumbelliferyl 2-acetamido-2-deoxy-4,6-O-di-tert-butylsilanediyl-β-D-glucopyranoside
• 英文别名: N-[(4aR,6S,7R,8R,8aS)-2,2-ditert-butyl-8-hydroxy-6-(4-methyl-2-oxochromen-7-yl)oxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3,2]dioxasilin-7-yl]acetamide
• CAS: 1319721-54-4
• 化学式: C₂₆H₃₇NO₈Si
• 分子量: 519.667
• InChiKey: VLPJUZWZFSMIQG-JTYPQFNSSA-N

物化性质

• 沸点：
  700.6±60.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.53
• 重原子数：
  36
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  113
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-methylumbelliferyl 2-acetamido-2-deoxy-4,6-O-di-tert-butylsilanediyl-β-D-glucopyranoside 在 二苯基亚砜 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  A practical synthesis of capped 4-methylumbelliferyl hyaluronan disaccharides and tetrasaccharides as potential hyaluronidase substrates

  摘要：

  The synthesis of hyaluronan dimers and tetramers equipped with a 4-methylumbelliferyl group at the reducing end to potentially allow monitoring of hyaluronidase activities is described. The 4-OH at the non-reducing glucuronate in the presented series is either removed or methylated to prohibit transglycosylase reactions, leading to a total of four probes. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.03.042
• 作为产物：
  描述：

  2-乙酰氨基-3,4,6-三-O-乙酰-2-脱氧-α-D-吡喃葡萄糖酰基氯 在 cesium hydroxide 、 四丁基溴化铵 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.84h， 生成 4-methylumbelliferyl 2-acetamido-2-deoxy-4,6-O-di-tert-butylsilanediyl-β-D-glucopyranoside
  参考文献：
  名称：

  A practical synthesis of capped 4-methylumbelliferyl hyaluronan disaccharides and tetrasaccharides as potential hyaluronidase substrates

  摘要：

  The synthesis of hyaluronan dimers and tetramers equipped with a 4-methylumbelliferyl group at the reducing end to potentially allow monitoring of hyaluronidase activities is described. The 4-OH at the non-reducing glucuronate in the presented series is either removed or methylated to prohibit transglycosylase reactions, leading to a total of four probes. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.03.042

文献信息

• A practical synthesis of capped 4-methylumbelliferyl hyaluronan disaccharides and tetrasaccharides as potential hyaluronidase substrates
  作者：Henrik Gold、Stefan Munneke、Jasper Dinkelaar、Herman S. Overkleeft、Johannes M.F.G. Aerts、Jeroen D.C. Codée、Gijs A. van der Marel

  DOI：10.1016/j.carres.2011.03.042

  日期：2011.9

  The synthesis of hyaluronan dimers and tetramers equipped with a 4-methylumbelliferyl group at the reducing end to potentially allow monitoring of hyaluronidase activities is described. The 4-OH at the non-reducing glucuronate in the presented series is either removed or methylated to prohibit transglycosylase reactions, leading to a total of four probes. (C) 2011 Elsevier Ltd. All rights reserved.