2-(2-trifluoroacetamidoethoxy)ethyl (2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-(1→4)-2,3-di-O-benzoyl-6-6-deoxy-6-methylseleno-β-D-glucopyranoside | 1595122-07-8

• 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: 2-(2-trifluoroacetamidoethoxy)ethyl (2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-(1→4)-2,3-di-O-benzoyl-6-6-deoxy-6-methylseleno-β-D-glucopyranoside
• CAS: 1595122-07-8
• 化学式: C₆₁H₅₆F₃NO₁₈Se
• 分子量: 1227.07
• InChiKey: BRISHUNBGHTVKP-RBQCBCIHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.69
• 重原子数：
  84.0
• 可旋转键数：
  24.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  233.05
• 氢给体数：
  1.0
• 氢受体数：
  18.0

反应信息

• 作为产物：
  描述：

  (2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-(1→4)-2,3-di-O-benzoyl-6-deoxy-6-methylseleno-D-glucopyranosyl trichloroacetimidate 、 2-(2-trifluoroacetamidoethoxy)ethanol 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 9.0h， 以66%的产率得到2-(2-trifluoroacetamidoethoxy)ethyl (2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-(1→4)-2,3-di-O-benzoyl-6-6-deoxy-6-methylseleno-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