methyl 3-O-(4-iodobenzyl)-β-D-galactopyranoside | 909706-80-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-O-(4-iodobenzyl)-β-D-galactopyranoside
• 英文别名: (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-4-[(4-iodophenyl)methoxy]-6-methoxyoxane-3,5-diol
• CAS: 909706-80-5
• 化学式: C₁₄H₁₉IO₆
• 分子量: 410.206
• InChiKey: AAIFCPBIHQZJAF-XHJNMGKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  88.4
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 3-O-(4-iodobenzyl)-β-D-galactopyranoside 在 吡啶 作用下， 反应 2.0h， 生成
  参考文献：
  名称：

  Cobalt-mediated solid phase synthesis of 3-O-alkynylbenzyl galactosides and their evaluation as galectin inhibitors

  摘要：

  Methyl beta-D-galactoside was converted to the corresponding 3,4-O-stannylene acetal, which was selectively benzylated with 3-iodobenzyl bromide and coupled to a polymer-bound propargylic ether via a Sonogashira reaction. The polymer-bound carbohydrate substrate was cleaved from the resin with different carbon nucleophiles in a cobalt-mediated Nicholas reaction. The product 3-O-alkynylbenzyl galactosides were screened towards galectin-1, -3, -7, -8N and -9N in a competitive fluorescence polarisation assay. Particularly potent inhibitors were identified against galectin-7 with affinity enhancements up to one order of magnitude due to the 3-O-alkynylbenzyl moiety. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.06.057
• 作为产物：
  描述：

  4-碘苄基溴 、 甲基-Β-D-吡喃半乳糖苷 在 二正丁基氧化锡 、 四丁基溴化铵 作用下， 以 甲醇 、 1,4-二氧六环 为溶剂， 反应 2.0h， 以64%的产率得到methyl 3-O-(4-iodobenzyl)-β-D-galactopyranoside
  参考文献：
  名称：

  Cobalt-mediated solid phase synthesis of 3-O-alkynylbenzyl galactosides and their evaluation as galectin inhibitors

  摘要：

  Methyl beta-D-galactoside was converted to the corresponding 3,4-O-stannylene acetal, which was selectively benzylated with 3-iodobenzyl bromide and coupled to a polymer-bound propargylic ether via a Sonogashira reaction. The polymer-bound carbohydrate substrate was cleaved from the resin with different carbon nucleophiles in a cobalt-mediated Nicholas reaction. The product 3-O-alkynylbenzyl galactosides were screened towards galectin-1, -3, -7, -8N and -9N in a competitive fluorescence polarisation assay. Particularly potent inhibitors were identified against galectin-7 with affinity enhancements up to one order of magnitude due to the 3-O-alkynylbenzyl moiety. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.06.057