2 research outputs found
Glycosidation of Thioglycosides in the Presence of Bromine: Mechanism, Reactivity, and Stereoselectivity
Elaborating on previous studies by Lemieux for highly
reactive
“armed” bromides, we discovered that β-bromide
of the superdisarmed (2-<i>O</i>-benzyl-3,4,6-tri-<i>O</i>-benzoyl) series can be directly obtained from the thioglycoside
precursor. When this bromide is glycosidated, α-glycosides form
exclusively; however, the yields of such transformations may be low
due to the competing anomerization into α-bromide that is totally
unreactive under the established reaction conditions
A Concise Synthesis of the Repeating Unit of Capsular Polysaccharide <i>Staphylococcus aureus</i> Type 8
The
first synthesis of the repeating unit of <i>S. aureus</i> capsular polysaccharide type 8 is described. The repeating unit
is an unusual trisaccharide sequence of three uncommon sugars, all
connected via 1,2-<i>cis</i> linkages. The synthetic trisaccharide
was equipped with capping methyl groups at the points of propagation
of the polysaccharide sequence