Catalytic approaches to chemo-and site-selective transformation of carbohydrates

K Yamatsugu, M Kanai - Chemical Reviews, 2023 - ACS Publications
Carbohydrates are a fundamental unit playing pivotal roles in all the biological processes. It
is thus essential to develop methods for synthesizing, functionalizing, and manipulating …

Site-selective functionalization of hydroxyl groups in carbohydrate derivatives

V Dimakos, MS Taylor - Chemical reviews, 2018 - ACS Publications
Methods for site-selective transformations of hydroxyl groups in carbohydrate derivatives are
reviewed. The construction of oligosaccharides of defined connectivity hinges on such …

“One-pot” protection, glycosylation, and protection–glycosylation strategies of carbohydrates

SS Kulkarni, CC Wang, NM Sabbavarapu… - Chemical …, 2018 - ACS Publications
Carbohydrates, which are ubiquitously distributed throughout the three domains of life, play
significant roles in a variety of vital biological processes. Access to unique and …

Exploiting non-covalent interactions in selective carbohydrate synthesis

CCJ Loh - Nature Reviews Chemistry, 2021 - nature.com
Non-covalent interactions (NCIs) are a vital component of biological bond-forming events,
and have found important applications in multiple branches of chemistry. In recent years, the …

Regioselective acylation, alkylation, silylation and glycosylation of monosaccharides

J Lawandi, S Rocheleau, N Moitessier - Tetrahedron, 2016 - Elsevier
Many organisms use sugars as building blocks for more complex structures in nature such
as cellulose in plants and chitin in crustaceans. To construct these large polysaccharides …

Synthesis of carbohydrate building blocks via regioselective uniform protection/deprotection strategies

T Wang, AV Demchenko - Organic & biomolecular chemistry, 2019 - pubs.rsc.org
Discussed herein is the synthesis of partially protected carbohydrates by manipulating only
one type of a protecting group for a given substrate. The first focus of this review is the …

Catalytic Site-Selective Acylation of Carbohydrates Directed by Cation–n Interaction

G **ao, GA Cintron-Rosado, DA Glazier… - Journal of the …, 2017 - ACS Publications
Site-selective functionalization of hydroxyl groups in carbohydrates is one of the long-
standing challenges in chemistry. Using a pair of chiral catalysts, we now can differentiate …

The sugar cube: Network control and emergence in stereoediting reactions

HM Carder, G Occhialini, G Bistoni, C Riplinger… - Science, 2024 - science.org
Stereochemical editing strategies have recently enabled the transformation of readily
accessible substrates into rare and valuable products. Typically, site selectivity is achieved …

Zemplén transesterification: a name reaction that has misled us for 90 years

B Ren, M Wang, J Liu, J Ge, X Zhang, H Dong - Green Chemistry, 2015 - pubs.rsc.org
We demonstrated that using NaOH and NaOMe in methanol for deacylation are identical,
indicating that the Zemplén condition has been misleading us for almost 90 years. The …

Site‐Selective O‐Arylation of Glycosides

W Shang, ZD Mou, H Tang, X Zhang, J Liu… - Angewandte …, 2018 - Wiley Online Library
Direct and site‐selective O‐arylation of carbohydrates has been a challenge in synthesis.
Herein we report a method based on copper‐catalyzed O‐arylation to address this …