2-(trimethylsilyl)ethyl 2,3-di-O-benzoyl-6-deoxy-6-(pmethylbenzoylseleno)-β-D-galactopyranoside | 1595121-76-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(trimethylsilyl)ethyl 2,3-di-O-benzoyl-6-deoxy-6-(pmethylbenzoylseleno)-β-D-galactopyranoside
• CAS: 1595121-76-8
• 化学式: C₃₃H₃₈O₈SeSi
• 分子量: 669.705
• InChiKey: XKSQKXBUWMJHBX-SMWBDTCFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.15
• 重原子数：
  43.0
• 可旋转键数：
  12.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  108.36
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  2-(trimethylsilyl)ethyl 2,3-di-O-benzoyl-6-deoxy-6-(pmethylbenzoylseleno)-β-D-galactopyranoside 在 caesium carbonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 甲基肼 、 三氟乙酸 作用下， 以 吡啶 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 34.42h， 生成 2-(trimethylsilyl)ethyl (4-O-acetyl-2,3-di-O-benzoyl-6-deoxy-6-methylseleno-β-D-galactopyranosyl)-(1→4)-6-O-acetyl-2,3-di-O-(4-methoxybenzyl)-β-D-glucopyranoside
  参考文献：
  名称：

  Expanded potential of seleno-carbohydrates as a molecular tool for X-ray structural determination of a carbohydrate–protein complex with single/multi-wavelength anomalous dispersion phasing

  摘要：

  Seleno-lactoses have been successfully synthesized as candidates for mimicking carbohydrate ligands for human galectin-9 N-terminal carbohydrate recognition domain (NCRD). Selenium was introduced into the mono-or di-saccharides using p-methylselenobenzoic anhydride (Tol(2)Se) as a novel selenating reagent. The TolSe-substituted monosaccharides were converted into selenoglycosyl donors or acceptors, which were reacted with coupling partners to afford seleno-lactoses. The seleno-lactoses were converted to the target compounds. The structure of human galectin-9 NCRD co-crystallized with 6-MeSe-lactose was determined with single/multi-wavelength anomalous dispersion (SAD/MAD) phasing and was similar to that of the co-crystal with natural lactose. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.02.023
• 作为产物：
  描述：

  2-(trimethylsilyl)ethyl 2,3-di-O-benzoyl-β-D-galactopyranoside 在 哌啶 、 四溴化碳 、 N,N-二异丙基乙胺 、 三苯基膦 作用下， 以 吡啶 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.92h， 生成 2-(trimethylsilyl)ethyl 2,3-di-O-benzoyl-6-deoxy-6-(pmethylbenzoylseleno)-β-D-galactopyranoside
  参考文献：
  名称：

  Expanded potential of seleno-carbohydrates as a molecular tool for X-ray structural determination of a carbohydrate–protein complex with single/multi-wavelength anomalous dispersion phasing

  摘要：

  Seleno-lactoses have been successfully synthesized as candidates for mimicking carbohydrate ligands for human galectin-9 N-terminal carbohydrate recognition domain (NCRD). Selenium was introduced into the mono-or di-saccharides using p-methylselenobenzoic anhydride (Tol(2)Se) as a novel selenating reagent. The TolSe-substituted monosaccharides were converted into selenoglycosyl donors or acceptors, which were reacted with coupling partners to afford seleno-lactoses. The seleno-lactoses were converted to the target compounds. The structure of human galectin-9 NCRD co-crystallized with 6-MeSe-lactose was determined with single/multi-wavelength anomalous dispersion (SAD/MAD) phasing and was similar to that of the co-crystal with natural lactose. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.02.023