122204-64-2Relevant academic research and scientific papers
Glycosylation Reactions with Di-O-acetyl-2,6-dibromo-2,6-dideoxy-α-D-mannopyranosyl Bromide. A Simple Synthesis of Methyl 2,6-Dideoxy-D-arabino-hexopyranoside
Bock, Klaus,Lundt, Inge,Pedersen, Christian,Pedersen, Henrik
, p. 640 - 645 (2007/10/02)
Glycosylation reactions using 3,4-di-O-acetyl-2,6-dibromo-2,6-dideoxy-α-D-mannopyranosyl bromide (1) have been investigated.Glycosylation with methanol and acid gives a high yield of the two anomeric glycosides, which can be isolated by fractional crystallization and further converted into the corresponding 2,6-dideoxyglycosides in good yield.In contrast, Koenig-Knorr glycosylation reaction conditions give only moderate yields of the methyl glycosides and the products are always contaminated with substantial amounts of by-products, including a 1,3-orthoester derivative.Glycosylation reactions of 1 promoted by halide ions or mercury(II) iodide give α-glycosides in good yield without the formation of by-products.
