Department of Chemistry of Natural Compounds, Institute of Chemical Technology Prague, Technická 5, Prague 166 28, Czech Republic.
Carbohydr Res. 2012 Oct 1;360:31-9. doi: 10.1016/j.carres.2012.07.015. Epub 2012 Aug 2.
Two novel nonisosteric UDP-Gal analogues, (2-deoxy-2-fluoro- and 4-deoxy-4-fluoro-α-D-galactopyranosyl) phosphonoyl phosphates, were synthesized by optimized multistep procedures starting from 3,4,6-tri-O-benzyl-D-galactal and allyl 2,3,6-tri-O-benzyl-α-D-glucopyranoside, respectively. The key steps were a Michaelis-Arbuzov reaction of respective deoxy-fluoro-D-galactopyranosyl acetate with triethyl phosphite followed by a Moffatt-Khorana coupling reaction with UMP-morpholidate. The structure of all new compounds was confirmed by NMR and mass spectroscopies..
两种新型非同系物 UDP-Gal 类似物，（2-脱氧-2-氟-和 4-脱氧-4-氟-α-D-半乳糖吡喃糖基）膦酸酯，分别通过从 3,4,6-三-O-苄基-D-半乳糖醛和烯丙基 2,3,6-三-O-苄基-α-D-吡喃葡萄糖苷开始的优化多步程序合成。关键步骤是相应的脱氧-氟-D-半乳糖吡喃糖基乙酸酯与三乙基亚磷酸酯的 Michaelis-Arbuzov 反应，然后与 UMP-吗啉代的 Moffatt-Khorana 偶联反应。所有新化合物的结构均通过 NMR 和质谱法确认。
