4-methylumbelliferyl 2-acetamido-4,6-O-di-tert-butylsilandiyl-2-deoxy-3-O-(methyl 2,3-dibenzoyl-4-O-(4,6-O-di-tert-butylsilandiyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranosyl)-β-D-glucopyranosyluronate)-β-D-glucopyranoside | 1319721-67-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methylumbelliferyl 2-acetamido-4,6-O-di-tert-butylsilandiyl-2-deoxy-3-O-(methyl 2,3-dibenzoyl-4-O-(4,6-O-di-tert-butylsilandiyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranosyl)-β-D-glucopyranosyluronate)-β-D-glucopyranoside
• 英文别名: methyl (2S,3S,4S,5R,6R)-6-[[(4aR,6S,7R,8R,8aS)-7-acetamido-2,2-ditert-butyl-6-(4-methyl-2-oxochromen-7-yl)oxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3,2]dioxasilin-8-yl]oxy]-3-[[(4aR,6S,7R,8R,8aS)-2,2-ditert-butyl-8-hydroxy-7-[(2,2,2-trichloroacetyl)amino]-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3,2]dioxasilin-6-yl]oxy]-4,5-dibenzoyloxyoxane-2-carboxylate
• CAS: 1319721-67-9
• 化学式: C₆₃H₈₁Cl₃N₂O₂₁Si₂
• 分子量: 1364.87
• InChiKey: KRPCHYXGONOSKP-DZVCXHGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.69
• 重原子数：
  91
• 可旋转键数：
  20
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  276
• 氢给体数：
  3
• 氢受体数：
  21

反应信息

• 作为反应物：
  描述：

  methyl (2,3-di-O-benzoyl-4-O-methyl-α/β-D-glucopyranoside N-phenyl-2,2,2-trifluoroacetimidate)uronate 、 4-methylumbelliferyl 2-acetamido-4,6-O-di-tert-butylsilandiyl-2-deoxy-3-O-(methyl 2,3-dibenzoyl-4-O-(4,6-O-di-tert-butylsilandiyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranosyl)-β-D-glucopyranosyluronate)-β-D-glucopyranoside 在 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以85%的产率得到4-methylumbelliferyl 2-acetamido-4,6-O-di-tert-butylsilandiyl-2-deoxy-3-O-{methyl 2,3-dibenzoyl-4-O-[4,6-O-di-tert-butylsilandiyl-2-deoxy-3-O-(methyl 2,3-di-O-benzoyl-4-O-methyl-β-D-glucopyranosyl uronate)-2-trichloroacetamido-β-D-glucopyranosyl]-β-D-glucopyranosyl uronate}-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
• 作为产物：
  描述：

  4-methylumbelliferyl 2-acetamido-4,6-O-di-tert-butylsilandiyl-2-deoxy-3-O-(methyl 2,3-dibenzoyl-4-O-(4,6-O-di-tert-butylsilandiyl-2-deoxy-3-O-levulinoyl-2-trichloroacetamido-β-D-glucopyranosyl)-β-D-glucopyranosyluronate)-β-D-glucopyranoside 在 肼 作用下， 以 吡啶 、 溶剂黄146 为溶剂， 反应 0.17h， 以99%的产率得到4-methylumbelliferyl 2-acetamido-4,6-O-di-tert-butylsilandiyl-2-deoxy-3-O-(methyl 2,3-dibenzoyl-4-O-(4,6-O-di-tert-butylsilandiyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranosyl)-β-D-glucopyranosyluronate)-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