methyl (2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-(1→4)-2,3,6-tri-O-benzoyl-1-seleno-β-D-glucopyranoside | 1595121-41-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-(1→4)-2,3,6-tri-O-benzoyl-1-seleno-β-D-glucopyranoside
• CAS: 1595121-41-7
• 化学式: C₆₂H₅₂O₁₇Se
• 分子量: 1148.04
• InChiKey: XNQDPBLVFNKYPD-BEEKPZMTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.42
• 重原子数：
  80.0
• 可旋转键数：
  19.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  211.79
• 氢给体数：
  0.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  methyl (2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-(1→4)-2,3,6-tri-O-benzoyl-1-seleno-β-D-glucopyranoside 在 甲醇 、 sodium methylate 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以88%的产率得到methyl (β-D-galactopyranosyl)-(1→4)-1-seleno-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：

  p-methylbenzoyl (2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-(1→4)-2,3,6-tri-O-benzoyl-1-seleno-β-D-glucopyranoside 、 碘甲烷 在 caesium carbonate 、 甲基肼 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.67h， 以99%的产率得到methyl (2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-(1→4)-2,3,6-tri-O-benzoyl-1-seleno-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