17371-38-9Relevant articles and documents
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.
Catalytic and regioselective oxidation of carbohydrates to synthesize keto-sugars under mild conditions
Muramatsu, Wataru
supporting information, p. 4846 - 4849 (2015/04/27)
A new catalytic and regioselective approach for the synthesis of keto-sugars is described. An organotin catalyst, Oc2SnCl2, in the presence of trimethylphenylammonium tribromide ([TMPhA]+Br3-) accelerates the regioselective oxidation at the axial -OH group of 1,2-diol moieties in galactopyranosides. The reaction conditions can also be used for the regioselective oxidation of various carbohydrates.
