Rösch Alexander, Kunz Horst
Institut für Organische Chemie, Johannes Gutenberg-Universität Mainz, Duesbergweg 10-14, D-55128 Mainz, Germany.
Carbohydr Res. 2006 Jul 24;341(10):1597-608. doi: 10.1016/j.carres.2006.03.003. Epub 2006 Apr 11.
Using the stannylene method, the trisaccharide 2-acetamido-3-O-[6-O-benzyl-beta-D-galactopyranosyl]-4-O-[2,3,4-tri-O-benzyl-beta-D-arabinopyranosyl]-6-O-benzyl-2-deoxy-beta-D-glucopyranosyl azide was regioselectively sulfonated and, after reduction of the anomeric azide, coupled to Fmoc alpha-allyl aspartate. After Pd(0)-catalyzed deallylation, the sulfatyl Lewis(a) asparagine building block was obtained, suitable for solid-phase glycopeptide synthesis applying the fluoride labile PTMSEL linker system.
采用亚锡烯法，对三糖2-乙酰氨基-3-O-[6-O-苄基-β-D-吡喃半乳糖基]-4-O-[2,3,4-三-O-苄基-β-D-吡喃阿拉伯糖基]-6-O-苄基-2-脱氧-β-D-吡喃葡萄糖基叠氮化物进行区域选择性磺化，在还原异头叠氮化物后，与Fmocα-烯丙基天冬氨酸偶联。经钯(0)催化脱烯丙基反应后，得到硫酸化路易斯(a)天冬酰胺构建块，适用于应用氟化物不稳定的PTMSEL连接子系统进行固相糖肽合成。
