• 10.1039/b702551c
  • Chem. Commun.
  • January 2007
  • pp 2336-2338

Efficient, one-pot syntheses of biologically active α-linked glycolipids

Adjustments needed to increase efficiency of methodology


The methodology described in this article is very valuable for scientists working with glycosphingolipids. It provided a one-pot syntheses of alpha-linked glycolipids with the possibility of using substrates with unsaturations in the fatty acid side chains. This was a challenge when benzyl protecting groups were present and their cleavage was effected under hydrogenation conditions. Although this is a great method, some ajustments to the experimental section would make this methodology more efficient and broad. First, additional equivalents of sugar (donor) were added after 24 hr (to drive the reaction to completion). In the procedure described in the article, only 3 equivalents were used; however we usually added up to 5 equivalents. Also, while trying to reproduce their results, we found that the work-up described in the article should have included an effective method to remove tetrabutylammonium iodide (TBAI) from the crude reaction mixture. In the experimental section, only chromatography was performed after silyl cleavage. We found that to obtain pure glycolipid, before cleaving the silyl protecting groups (TMS), the crude mixture should be washed with 1:1, ethyl acetate:hexanes. After cleavage, the deprotected product was purified by chromatography. This was the best procedure to obtain pure product and reasonable yield (30%). Without this modification, our yields of the glycolipid products were very low (~5%).

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