Methods for 2-deoxyglycoside synthesis

CS Bennett, MC Galan - Chemical reviews, 2018 - ACS Publications
Deoxy-sugars often play a critical role in modulating the potency of many bioactive natural
products. Accordingly, there has been sustained interest in methods for their synthesis over …

Catalytic glycosylations in oligosaccharide synthesis

MM Nielsen, CM Pedersen - Chemical reviews, 2018 - ACS Publications
Catalytic glycosylation has been a central reaction in carbohydrate chemistry since its
introduction by Fischer 125 years ago, but it is only in the past three to four decades that …

Stereocontrolled 1, 2-cis glycosylation as the driving force of progress in synthetic carbohydrate chemistry

SS Nigudkar, AV Demchenko - Chemical science, 2015 - pubs.rsc.org
Recent developments in stereoselective 1, 2-cis glycosylation that have emerged during the
past decade are surveyed herein. For detailed coverage of the previous achievements in the …

ortho-Methoxycarbonylethynylphenyl Thioglycosides (MCEPTs): Versatile Glycosyl Donors Enabled by Electron-Withdrawing Substituents and Catalyzed by Gold(I) …

H Liu, ZF Liang, HJ Liu, JX Liao, LJ Zhong… - Journal of the …, 2023 - ACS Publications
With easily accessible and operator-friendly reagents, shelf-stable ortho-
methoxycarbonylethynylphenyl thioglycosides were efficiently prepared. Based on these …

Chemical O‐Glycosylations: An Overview

R Das, B Mukhopadhyay - ChemistryOpen, 2016 - Wiley Online Library
The development of glycobiology relies on the sources of particular oligosaccharides in their
purest forms. As the isolation of the oligosaccharide structures from natural sources is not a …

Efficient and versatile formation of glycosidic bonds via catalytic strain-release glycosylation with glycosyl ortho−2,2-dimethoxycarbonylcyclopropylbenzoate donors

H Ding, J Lyu, XL Zhang, X Xiao, XW Liu - Nature Communications, 2023 - nature.com
Catalytic glycosylation is a vital transformation in synthetic carbohydrate chemistry due to its
ability to expediate the large-scale oligosaccharide synthesis for glycobiology studies with …

Gold-catalyzed glycosylation in the synthesis of complex carbohydrate-containing natural products

W Li, B Yu - Chemical Society Reviews, 2018 - pubs.rsc.org
The methodological developments in gold (I)-and gold (III)-catalyzed glycosylation reactions
are fully surveyed, which exploit the special alkynophilicity or the Lewis acidity of the gold …

A Visible‐Light‐Promoted O‐Glycosylation with a Thioglycoside Donor

ML Spell, K Deveaux, CG Bresnahan… - Angewandte Chemie …, 2016 - Wiley Online Library
Visible‐light irradiation of 4‐p‐methoxyphenyl‐3‐butenylthioglucoside donors in the
presence of Umemoto's reagent and alcohol acceptors serves as a mild approach to O …

Gold (I)-catalyzed direct stereoselective synthesis of deoxyglycosides from glycals

C Palo-Nieto, A Sau, MC Galan - Journal of the American …, 2017 - ACS Publications
Au (I) in combination with AgOTf enables the unprecedented direct and α-stereoselective
catalytic synthesis of deoxyglycosides from glycals. Mechanistic investigations suggest that …

Recent advances in direct synthesis of 2-deoxy glycosides and thioglycosides

S Meng, X Li, J Zhu - Tetrahedron, 2021 - Elsevier
Deoxy sugars exist in numerous bioactive molecules and exert significant influences on their
physical, chemical, and biological properties. Due to the absence of directing group at C-2 …