2-(trimethylsilyl)ethyl (β-D-galactopyranosyl)-(1→4)-6-deoxy-6-methylseleno-β-D-glucopyranoside | 1595121-25-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(trimethylsilyl)ethyl (β-D-galactopyranosyl)-(1→4)-6-deoxy-6-methylseleno-β-D-glucopyranoside
• 英文别名: 2-(Trimethylsilyl)ethyl 4-O-Beta-D-Galactopyranosyl-6-Se-Methyl-6-Seleno-Beta-D-Glucopyranoside；(2S,3R,4S,5R,6R)-2-[(2S,3S,4R,5R,6R)-4,5-dihydroxy-2-(methylselanylmethyl)-6-(2-trimethylsilylethoxy)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 1595121-25-7
• 化学式: C₁₈H₃₆O₁₀SeSi
• 分子量: 519.523
• InChiKey: DAHDBHYUNUXOAL-MUKCROHVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.86
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  158
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  2-(trimethylsilyl)ethyl (2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-(1→4)-6-deoxy-6-methylseleno-β-D-glucopyranoside 在 甲醇 、 sodium methylate 作用下， 以 四氢呋喃 为溶剂， 反应 5.5h， 以100%的产率得到2-(trimethylsilyl)ethyl (β-D-galactopyranosyl)-(1→4)-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