Harris J M, Keränen M D, Nguyen H, Young V G, O'Doherty G A
Department of Chemistry, University of Minnesota, Minneapolis 55455, USA.
Carbohydr Res. 2000 Aug 18;328(1):17-36. doi: 10.1016/s0008-6215(00)00031-8.
An expeditious approach to various protected hexoses has been developed by the use of the Sharpless catalytic asymmetric dihydroxylation reaction. Applying the Sharpless catalytic asymmetric dihydroxylation reaction on vinylfuran, diols with high enantioexcess are produced. The resulting diols can be stereoselectively transformed into either protected D- or L-mannose in five steps and approximately 39% yield from furfural. Similarly, both D- and L-talose and gulose have been synthesized in 19% overall yields, respectively. Using a modified strategy, both protected D- and L-gulo- and allo-sugar-delta-lactones were synthesized in eight steps and approximately 20%, overall yield from furfural.
通过使用夏普莱斯催化不对称双羟基化反应，已开发出一种快速合成各种保护己糖的方法。将夏普莱斯催化不对称双羟基化反应应用于乙烯基呋喃，可生成具有高对映体过量的二醇。所得二醇可通过五步反应立体选择性地转化为保护的D-或L-甘露糖，从糠醛出发的产率约为39%。类似地，D-和L-塔罗糖以及古洛糖的合成总产率分别为19%。采用改进策略，通过八步反应合成了保护的D-和L-古洛糖以及阿洛糖-δ-内酯，从糠醛出发的总产率约为20%。
