α-Selective synthesis of 2-deoxy-glycosides and disaccharides

GRAPHICAL ABSTRACT

ABSTRACT

A metal-free catalytic method for the synthesis of 2-deoxy glycosides and disaccharides has been developed using stable 2-deoxy glucosyl and galactosyl acetate donors. They could react with a variety of acceptors in the presence of catalytic amount of TMSOTf at 0°C to form glycosides, glycoconjugates, and disaccharides with excellent α-selectivity (> 19:1) and yields (up to 99%) in a short time (0.5 h). With this expedient method, several new compounds against human K562 and SMMC7721 cell lines were obtained and tested with in vitro antitumor bioactivities.

KEYWORDS:

• 2-deoxy glycosides
• 2-deoxy disaccharides
• TMSOTf
• α-selective glycosylation
• antitumor activity

Acknowledgements

We thank the analytic center of East China Normal University for data measurement. The project was supported by Natural Science Foundation of Shanghai (11ZR1410400), “DAXIA” Foundation of East China Normal University (2011DX-084) and large instruments Open Foundation of East China Normal University (20151043&20162015).

Additional information

Funding

Natural Science Foundation of Shanghai [11ZR1410400]; “DAXIA” Foundation of East China Normal University [2011DX-084]; large instruments Open Foundation of East China Normal University [20151043, 20162015].