4163-45-5Relevant articles and documents
Elemental fluorine. Part 5. Reactions of 1,3-dithiolanes and thioglycosides with fluorine-iodine mixtures
Chambers, Richard D.,Sandford, Graham,Sparrowhawk, Matthew E.,Atherton, Malcolm J.
, p. 1941 - 1944 (1996)
1,3-Dithiolanes, prepared from diaryl ketones, react with elemental fluorine-iodine mixtures to give the corresponding difluoromethylene derivatives. Under the same conditions, thioglycosides give glycosyl fluorides in good yields. Reaction of 1,3-dithiolanes with fluorine in aqueous acetonitrile provides a remarkably mild method for efficient deprotection to the parent ketone.
A Substituent-Directed Strategy for the Selective Synthesis of L-Hexoses: An Expeditious Route to L-Idose
See, Nicholas W.,Wimmer, Norbert,Krenske, Elizabeth H.,Ferro, Vito
, p. 1575 - 1584 (2021/03/03)
L-Hexoses are rare but biologically significant components of various important biomolecules. However, most are prohibitively expensive (if commercially available) which limits their study and biotechnological exploitation. New, efficient methods to access L-hexoses and their derivatives are thus of great interest. In a previous study, we showcased a stereoselective Bu3SnH-mediated transformation of a 5-C-bromo-D-glucuronide to an L-iduronide. We have now drawn inspiration from this result to derive a new methodology – one that can be harnessed to access other L-hexoses. DFT calculations demonstrate that a combination of a β-F at the anomeric position and a methoxycarbonyl substituent at C-6 is key to optimising the selectivity for the L-hexose product. Our investigations have also culminated in the development of the shortest known synthetic route to a derivative of L-idose from a commercially available starting material (45 % yield over 3 steps). Collectively, these results address the profound lack of understanding of how to synthesise L-hexoses in a stereoselective fashion.
Chemical glucosylation of pyridoxine
Bachmann, Thomas,Rychlik, Michael
, (2020/02/13)
The chemical synthesis of pyridoxine-5′-β-D-glucoside (5′-β-PNG) was investigated using various glucoside donors and promoters. Hereby, the combination of α4,3-O-isopropylidene pyridoxine, glucose vested with different leaving and protecting groups and the application of stoichiometric amounts of different promoters was examined with regards to the preparation of the twofold protected PNG. Best results were obtained with 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl fluoride and boron trifluoride etherate (2.0 eq.) as promoter at 0 °C (59%). The deprotection was accomplished stepwise with potassium/sodium hydroxide in acetonitrile/water followed by acid hydrolysis with formic acid resulting in the chemical synthesis of 5′-β-PNG.
