72946-46-4Relevant academic research and scientific papers
Glycosidation of thioglycosides in the presence of bromine: Mechanism, reactivity, and stereoselectivity
Kaeothip, Sophon,Yasomanee, Jagodige P.,Demchenko, Alexei V.
experimental part, p. 291 - 299 (2012/03/08)
Elaborating on previous studies by Lemieux for highly reactive "armed" bromides, we discovered that β-bromide of the superdisarmed (2-O-benzyl-3,4,6-tri-O-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.
Glycosyl alkoxythioimidates as complementary building blocks for chemical glycosylation
Ranade, Sneha C.,Kaeothip, Sophon,Demchenko, Alexei V.
supporting information; experimental part, p. 5628 - 5631 (2011/03/20)
It is reported that S-glycosyl O-methyl phenylcarbamothioates (SNea carbamothioates) have a fully orthogonal character in comparison to S-benzoxazolyl (SBox) glycosides. This complete orthogonality was revealed by performing competitive glycosylation expe
An expedient route to acylated glucosyl halides with a free 2-OH group
Lichtenthaler, Frieder W.,Koehler, Bernd
, p. 77 - 86 (2007/10/02)
The carbonyl group of 3,4,6-tri-O-benzoyl-α-D-arabino-hexosyl-2-ulose bromide (8), readily accessible from the hydroxyglycal ester, can be reduced by cyanoborohydride without affecting the anomeric bromine; exclusive axial attack of the hydride affords th
