Synthesis and glycosidation of anomeric halides: evolution from early studies to modern methods of the 21st century

Y Singh, SA Geringer, AV Demchenko - Chemical reviews, 2022 - ACS Publications
Advances in synthetic carbohydrate chemistry have dramatically improved access to
common glycans. However, many novel methods still fail to adequately address challenges …

1, 2-Diacetals: a new opportunity for organic synthesis

SV Ley, DK Baeschlin, DJ Dixon, AC Foster… - Chemical …, 2001 - ACS Publications
While 1, 2-diacetals have been known in the literature since 1938, 1 their specific
application in organic synthesis has been recognized only recently. It seems remarkable to …

Mechanistic studies and methods to prevent aglycon transfer of thioglycosides

Z Li, JC Gildersleeve - Journal of the American Chemical Society, 2006 - ACS Publications
Thioglycosides have been employed extensively for the synthesis of complex
oligosaccharides, carbohydrate libraries, and mimetics of O-glycosides. While very useful …

Aromatic O-glycosylation

M Jacobsson, J Malmberg, U Ellervik - Carbohydrate research, 2006 - Elsevier
Carbohydrates carrying an aromatic aglycon are important natural products and thus key
synthetic targets. However, due to the electron-withdrawing properties of aromatic rings …

First principles insight into the α-glucan structures of starch: their synthesis, conformation, and hydration

I Damager, SB Engelsen, A Blennow… - Chemical …, 2010 - ACS Publications
Carbohydrates constitute the most abundant group of organic compounds found in nature.
Oxygenic photosynthesis, the process energizing carbon dioxide fixation in the biosphere, is …

Glycosyl disulfides: novel glycosylating reagents with flexible aglycon alteration

EJ Grayson, SJ Ward, AL Hall, PM Rendle… - The Journal of …, 2005 - ACS Publications
Glycosyl disulfides have been shown for the first time to be effective glycosyl donors.
Glucosylation and galactosylation of a panel of representative alcohol acceptors allowed the …

Koenigs–Knorr glycosylation reaction catalyzed by trimethylsilyl trifluoromethanesulfonate

Y Singh, AV Demchenko - Chemistry–A European Journal, 2019 - Wiley Online Library
The discovery that traditional silver (I)‐oxide‐promoted glycosidations of glycosyl bromides
(Koenigs–Knorr reaction) can be greatly accelerated in the presence of catalytic …

Defining the Scope of the Acid‐Catalyzed Glycosidation of Glycosyl Bromides

Y Singh, AV Demchenko - Chemistry–A European Journal, 2020 - Wiley Online Library
Following the recent discovery that traditional silver (I) oxide‐promoted glycosidations of
glycosyl bromides (Koenigs–Knorr reaction) can be greatly accelerated in the presence of …

Observations on the activation of methyl thioglycosides by iodine and its interhalogen compounds

KPR Kartha, P Cura, M Aloui, SK Readman… - Tetrahedron …, 2000 - Elsevier
Treatment of 'armed'methyl thiogalactosides with iodine in the absence of an acceptor
alcohol results in thioglycoside epimerisation, whereas there is no effect on the …

Reaction of 1, 2-trans-glycosyl acetates with phosphorus pentachloride: new efficient approach to 1, 2-trans-glycosyl chlorides

FM Ibatullin, SI Selivanov - Tetrahedron letters, 2002 - Elsevier
Reaction of phosphorus pentachloride with 1, 2-trans-glycosyl esters is described. The
reaction mechanism presumably involves formation of a tetrachlorophosphonium ion as one …