12-acetylthiododecyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-acetyl-2-deoxy-α-D-arabino-hexopyranoside | 1277170-73-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 12-acetylthiododecyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-acetyl-2-deoxy-α-D-arabino-hexopyranoside
• 英文别名: [(2R,3S,4R,6S)-4-acetyloxy-6-(12-acetylsulfanyldodecoxy)-3-[(2S,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 1277170-73-6
• 化学式: C₃₈H₆₀O₁₇S
• 分子量: 820.95
• InChiKey: XWFRYMBRKONCHB-RZHRDYCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  56
• 可旋转键数：
  31
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  237
• 氢给体数：
  0
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  12-acetylthiododecyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-acetyl-2-deoxy-α-D-arabino-hexopyranoside 在 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 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
• 作为产物：
  描述：

  12-溴-1-十二烷醇 在 三苯基膦氢溴酸盐 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 12-acetylthiododecyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)- 3,6-di-O-acetyl-2-deoxy-β-D-arabino-hexopyranoside 、 12-acetylthiododecyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-acetyl-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