Al-Mughaid Hussein, Grindley T Bruce
Department of Chemistry, Dalhousie University, Halifax, Nova Scotia, B3H 4J3 Canada.
J Org Chem. 2006 Feb 17;71(4):1390-8. doi: 10.1021/jo052045u.
A nonavalent glycodendrimer bearing terminal alpha-d-mannopyranoside units has been synthesized with a convergent approach. Terminal trivalent mannoside dendrons bearing p-halophenyl ethers were prepared by glycosylation of pentaerythritol derivatives having three 2-hydroxyethyl ether substituents. Two efficient routes were developed for the synthesis of the pentaerythritol-based core (17), which has three terminal propargyl ethers. Conditions were found under which the triple Sonogashira coupling reaction of the dendron and the tri-O-propargyl ether (17) proceeded efficiently. The product was deprotected and it and precursors were fully characterized by NMR spectroscopy and FT-ICR mass spectrometry.
通过汇聚法合成了一种带有末端α-D-甘露吡喃糖苷单元的九价糖树枝状大分子。通过对具有三个2-羟乙基醚取代基的季戊四醇衍生物进行糖基化反应，制备了带有对卤苯醚的末端三价甘露糖苷树枝单元。开发了两条有效的路线来合成具有三个末端炔丙基醚的季戊四醇基核心（17）。发现了树枝单元与三-O-炔丙基醚（17）的三Sonogashira偶联反应能有效进行的条件。产物进行了脱保护，其及前体通过核磁共振光谱和傅里叶变换离子回旋共振质谱进行了全面表征。
