Haukaas M H, O'Doherty G A
Department of Chemistry, University of Minnesota, Minneapolis, MN 55455, USA.
Org Lett. 2001 Nov 29;3(24):3899-902. doi: 10.1021/ol016743m.
The enantioselective synthesis of three 6-amino-6-deoxy sugars has been achieved in six to eight steps from furfural. A sequence of diastereoselective oxidation and reduction reactions produced Cbz-protected 6-aminomannose from furfuryl alcohol 3. The incorporation of a Mitsunobu reaction into the reaction sequence allows for the selective synthesis of both N-Cbz-protected 6-aminotalose and 6-aminogulose. The overall procedure allows for the synthesis of either enantiomer of these three aminosugars. [reaction: see text]
以糠醛为原料，通过六至八步反应实现了三种6-氨基-6-脱氧糖的对映选择性合成。一系列非对映选择性氧化和还原反应从糠醇3制得Cbz保护的6-氨基甘露糖。将Mitsunobu反应引入反应序列可选择性合成N-Cbz保护的6-氨基塔罗糖和6-氨基古洛糖。整个过程能够合成这三种氨基糖的任意一种对映体。[反应：见正文]
