161254-85-9Relevant academic research and scientific papers
Synthesis of α-Glycopyranosides of D-Galactosamine and D-Glucosamine via Iodocyclization of Corresponding Glycals and Silver Tetrafluoroboranuide-Promoted Alkynylation at the Anomeric Centre
Leteux, Christine,Veyrieres, Alain
, p. 2647 - 2656 (2007/10/02)
Iodocyclization of O-stannylated D-galactal 1, followed by azide ion displacement, gave 1,6-anhydro-2-azido-2-deoxy-β-D-galactopyranose 9 in a expeditious way.Transformation into bromide 12 allowed coupling of various alkynyltributylstannanes in the presence of silver tetrafluoroboranuide (silver tetrafluoroborate), thus affording the corresponding α,β-C-(D-galactopyranosyl)alkynes 13 - 17.Application of this methodology to the D-gluco isomeric bromide 24 gave a C-(D-glucopyranosyl)octyne 25 with total α-stereoselectivity.Conventional deprotection and saturation of the acetylenic linkage led to C-octyl-α-glycopyranosides of D-galactosamine 20 and D-glucosamine 28.
