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Stereoselective Protection-Free Modification of 3‑Keto-saccharides

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journal contribution
posted on 07.07.2020, 22:04 by Nittert Marinus, Nabil Tahiri, Margherita Duca, L. M. C. Marc Mouthaan, Simona Bianca, Marco van den Noort, Bert Poolman, Martin D. Witte, Adriaan J. Minnaard
Unprotected 3-keto-saccharides have become readily accessible via site-selective oxidation, but their protection-free functionalization is relatively unexplored. Here we show that protecting groups are obsolete in a variety of stereoselective modifications of our model substrate methyl α-glucopyranoside. This allows the preparation of rare sugars and the installation of click handles and reactive groups. To showcase the applicability of the methodology, maltoheptaose has been converted into a chemical probe, and the rare sugar evalose has been synthesized.