67313-39-7

Upstream product

• 108-24-7 acetic anhydride 
• 59464-22-1 1,6-anhydro-2-azido-2-deoxy-3,4-di-O-benzyl-β-D-galactopyranose 
• 79781-68-3 1-O-acetyl-2-azido-3,4,6-tri-O-benzyl-2-desoxy-D-galactopyranose 
• 67313-36-4 1,6-anhydro-2-azido-2-deoxy-β-D-galactopyranose 
• 65371-89-3 1,6-anhydro-3,4-O-isopropylidene-2-azido-2-deoxy-β-D-galactopyranose 
• 161254-77-9 1,6-anhydro-2-deoxy-2-iodo-β-D-galactopyranose 

Relevant 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

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.

Glycosylphosphonates of 2-Amino-2-deoxy-aldoses. Synthesis of a Phosphonate Analogue of Lipid X

A preparation of glycosylphosphonates (27, 28, 36, 38, and 39) from 2-azido-2-deoxy-glycoses (26, 35, and 37) and the synthesis of the non-isosteric phosphonate analogue 3a of lipid X (2) are described.The 2-azido group was introduced by azidonitration.Tr