2595-38-2Relevant articles and documents
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Lichtenthaler,F.W.,Bambach,G.
, p. 1621 - 1624 (1972)
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Stereoselective Protection-Free Modification of 3-Keto-saccharides
Bianca, Simona,Duca, Margherita,Marinus, Nittert,Minnaard, Adriaan J.,Mouthaan, L. M. C. Marc,Poolman, Bert,Tahiri, Nabil,Van Den Noort, Marco,Witte, Martin D.
supporting information, (2020/07/24)
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.