Efficient stereocontrolled synthesis of C-glycosides using glycosyl donors substituted by propane 1,3-diyl phosphate as the leaving group

Polyphosphates and Pyrophosphates of Pentopyranoses and Pentofuranoses as Allosteric Effectors of Human Hemoglobin: Synthesis, Molecular Recognition, and Oxygen Release

“…Orientation of the anomeric phosphate was expected to be driven by the anomeric effect and the presence of the vicinal axial hydroxy group on C2. Indeed, the small 3 J H1,H2 value is well matched with the corresponding coupling constants of other a-1-O-phosphorylated l-rhamnopyranosides, [27,28] in constrast to b-anomers, [28,29] which show no coupling at all. The obtained perphosphorylated ester 2 was subjected to hydrogenolysis in the presence of palladium on carbon and excess triethylamine to give triethylammonium salt 3.…”

“…The a-anomer was also desilylated under the same conditions to give derivative 31. Further evidence for the aand b-orientation of these ribose anomers (28,29,14, and 31) was provided by 13 C NMR experiments. Thus, the C1 signal of the b-anomers is shifted downfield relative to the a-anomer (d = 101.9 ppm for 28 and 29, 101.5 ppm for 14, whereas it was 98.2 ppm for compound 31).…”

Improved preparation of 4(5)-aryl-2-(β-d-glucopyranosyl)-imidazoles, the most efficient glucose analogue inhibitors of glycogen phosphorylase

“…O-Perbenzylated D-glucopyranosyl cyanides both in aand b-congurations are known from the literature. [16][17][18][19] While the…”

Catalytic Glycosylations in Oligosaccharide Synthesis

“…The same results were found for arabinofuranosyl donors, giving rise to higher yields and a preference for the thermodynamic products when using a stoichiometric amount of TMSOTf compared to when a catalytic amount was employed . The catalytic activation of the propane-1,3-diyl phosphate donor was also reported for the synthesis of C -glycosides …”