bis[16-[4-O-(2-acetamido-2-deoxy-β-D-galactopyranosyl)-β-D-galactopyranosyloxy]hexadecanyl] disulfide | 211869-92-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: bis[16-[4-O-(2-acetamido-2-deoxy-β-D-galactopyranosyl)-β-D-galactopyranosyloxy]hexadecanyl] disulfide
• CAS: 211869-92-0
• 化学式: C₆₀H₁₁₂N₂O₂₂S₂
• 分子量: 1277.68
• InChiKey: CUTWJIUNLIYIBU-AXGMUJBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.86
• 重原子数：
  86.0
• 可旋转键数：
  47.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  374.8
• 氢给体数：
  14.0
• 氢受体数：
  24.0

反应信息

• 作为反应物：
  描述：

  bis[16-[4-O-(2-acetamido-2-deoxy-β-D-galactopyranosyl)-β-D-galactopyranosyloxy]hexadecanyl] disulfide 在 碳酸氢铵 、 1,4-二巯基-2,3-丁二醇 作用下， 以 水 为溶剂， 反应 18.0h， 以32%的产率得到N-{(2S,3R,4R,5R,6R)-2-[(2R,3R,4R,5R,6R)-4,5-Dihydroxy-2-hydroxymethyl-6-(16-mercapto-hexadecyloxy)-tetrahydro-pyran-3-yloxy]-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl}-acetamide
  参考文献：
  名称：

  The synthesis of 16-mercaptohexadecanyl glycosides for biosensor applications

  摘要：

  The P-k trisaccharide and the central disaccharide element of asialo GM(1) activated as their trichloroacetimidates were each used to glycosylate 16-(p-toluensulfonyloxy)hexadecanol 1. Displacement of the tosyl group by thiocyanate followed by sodium borohydride reduction and saponification afforded oligosaccharide 16-mercaptohexadecanyl glycosides that were isolated as the corresponding disulfides 6 and 17 unless oxygen was rigorously excluded from the solvents used for work-up. Dithiothreitol reduction of disulfides and subsequent isolation under an inert atmosphere with degassed solvents gave the thiols 7 and 18. Chemisorption of omega-glycosyl alkanethiols and alkanethiols onto gold electrodes produces self-assembled monolayers that can act as amperometric biosensors for the detection of proteins that bind to the immobilized oligosaccharide epitope. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00053-6
• 作为产物：
  描述：

  2-(三甲基硅烷基)乙基beta-吡喃半乳糖苷 在 palladium on activated charcoal 、 palladium hydroxide - carbon sodium tetrahydroborate 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 Ag-silicate on alumina 、 氢气 、 sodium hydride 、 对甲苯磺酸 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三氟乙酸 作用下， 以 吡啶 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， -15.0~80.0 ℃ 、17.2 MPa 条件下， 反应 121.25h， 生成 bis[16-[4-O-(2-acetamido-2-deoxy-β-D-galactopyranosyl)-β-D-galactopyranosyloxy]hexadecanyl] disulfide
  参考文献：
  名称：

  The synthesis of 16-mercaptohexadecanyl glycosides for biosensor applications

  摘要：

  The P-k trisaccharide and the central disaccharide element of asialo GM(1) activated as their trichloroacetimidates were each used to glycosylate 16-(p-toluensulfonyloxy)hexadecanol 1. Displacement of the tosyl group by thiocyanate followed by sodium borohydride reduction and saponification afforded oligosaccharide 16-mercaptohexadecanyl glycosides that were isolated as the corresponding disulfides 6 and 17 unless oxygen was rigorously excluded from the solvents used for work-up. Dithiothreitol reduction of disulfides and subsequent isolation under an inert atmosphere with degassed solvents gave the thiols 7 and 18. Chemisorption of omega-glycosyl alkanethiols and alkanethiols onto gold electrodes produces self-assembled monolayers that can act as amperometric biosensors for the detection of proteins that bind to the immobilized oligosaccharide epitope. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00053-6