(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-(1→4)-2,3-di-O-benzoyl-6-deoxy-6-methylseleno-β-D-glucopyranose | 1595122-11-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-(1→4)-2,3-di-O-benzoyl-6-deoxy-6-methylseleno-β-D-glucopyranose
• CAS: 1595122-11-4
• 化学式: C₅₅H₄₈O₁₆Se
• 分子量: 1043.94
• InChiKey: HGAJUGNBTOWRTL-VKDJYKRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.97
• 重原子数：
  72.0
• 可旋转键数：
  17.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  205.72
• 氢给体数：
  1.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  (2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-(1→4)-2,3-di-O-benzoyl-6-deoxy-6-methylseleno-β-D-glucopyranose 、 三氯乙腈 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以81.818%的产率得到
  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 6-deoxy-2,3-di-O-(pmethoxybenzyl)-6-methylseleno-β-D-glucopyranoside 在 吡啶 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 31.92h， 生成 (2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-(1→4)-2,3-di-O-benzoyl-6-deoxy-6-methylseleno-β-D-glucopyranose
  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