12-mercaptododecyl β-D-galactopyranosyl-(1->4)-2-deoxy-α-D-arabino-hexopyranoside | 1277170-75-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 12-mercaptododecyl β-D-galactopyranosyl-(1->4)-2-deoxy-α-D-arabino-hexopyranoside
• 英文别名: 12-Mercaptododecyl-beta-D-galactopyranosyl-(1->4)-2-deoxy-alpha-D-arabino-hexopyranoside；(2S,3R,4S,5R,6R)-2-[(2R,3S,4R,6S)-4-hydroxy-2-(hydroxymethyl)-6-(12-sulfanyldodecoxy)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 1277170-75-8
• 化学式: C₂₄H₄₆O₁₀S
• 分子量: 526.689
• InChiKey: XDAYRUFVBXUGIK-XMODHHRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  35
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  159
• 氢给体数：
  7
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  2,2',3,3',4',6,6'-七-O-乙酰基-alpha-D-乳糖基溴化物 在 sodium methylate 、 sodium acetate 、 三苯基膦氢溴酸盐 、 copper(II) sulfate 、 锌 作用下， 以 甲醇 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 20.0h， 生成 12-mercaptododecyl β-D-galactopyranosyl-(1->4)-2-deoxy-α-D-arabino-hexopyranoside
  参考文献：
  名称：

  Synthesis and galectin-binding activities of mercaptododecyl glycosides containing a terminal β-galactosyl group

  摘要：

  Mercaptododecyl glycosides containing a terminal beta-galactosyl group were prepared from D-galactose or from D-lactose via hexa-O-acetyl-lactal (10) as a key intermediate. Interactions of these glycolipids (5 kinds) and galectins (beta-galactoside binding lectins, 6 species) were evaluated by surface plasmon resonance (SPR) method. High binding responses were observed for the lactoside, 2-deoxy-lactoside, and lactosaminide with some galectins (Gal-3, -4, -8), whereas the galactoside and 2,3-dideoxy-lactoside showed low binding activities. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.12.049