69534-63-0Relevant academic research and scientific papers
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.
The fluorination (at C5) of some derivatives of D-glucose
Skelton, Brian W.,Stick, Robert V.,Stubbs, Keith A.,Watts, Andrew G.,White, Allan H.
, p. 345 - 353 (2007/10/03)
The photobromination of various per-esters of β-D-glucopyranose and α- and β-D-glucopyranosyl fluoride has yielded 5-bromo derivatives capable of conversion into the corresponding 5-fluorides. The best reagent for this conversion was found to be silver te
Radical-mediated bromination of carbohydrate derivatives: Searching for alternative reaction conditions without carbon tetrachloride
Czifrák, Katalin,Somsák, László
, p. 8849 - 8852 (2007/10/03)
KBrO3-Na2S2O4 in CH2Cl2-H2O or PhCF3-H2O biphasic solvent systems was applied to the bromination of several monosaccharide derivatives having capto-datively
Photo-bromination of Carbohydrate Derivatives. Part 3. C-5 Bromination of Penta-O-benzoyl-α- and β-D-glucopyranose; a Route to D-xylo-Hexos-5-ulose Derivatives and α-L-Idopyranosides
Ferrier, Robert J.,Tyler, Peter C.
, p. 1528 - 1534 (2007/10/02)
Photo-bromination of penta-O-benzoyl-β-D-glucopyranose with bromine gives good yields of the 5-bromo-derivative; the α-anomer reacts less well but also gives a crystalline 5-bromide.Hydrolysis gives D-xylo-hexos-5-ulose tetrabenzoate, which exists as the
