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 …

Catalytic glycosylation for minimally protected donors and acceptors

QD Dang, YH Deng, TY Sun, Y Zhang, J Li, X Zhang… - Nature, 2024 - nature.com
Oligosaccharides have myriad functions throughout biological processes,. Chemical
synthesis of these structurally complex molecules facilitates investigation of their functions …

Diastereoselective Synthesis of Aryl C‐Glycosides from Glycosyl Esters via C−O Bond Homolysis

Y Wei, B Ben‐zvi, T Diao - Angewandte Chemie, 2021 - Wiley Online Library
C‐aryl glycosyl compounds offer better in vivo stability relative to O‐and N‐glycoside
analogues. C‐aryl glycosides are extensively investigated as drug candidates and applied …

Highly selective β-mannosylations and β-rhamnosylations catalyzed by bis-thiourea

Q Li, SM Levi, EN Jacobsen - Journal of the American Chemical …, 2020 - ACS Publications
We report highly β-selective bis-thioureas-catalyzed 1, 2-cis-O-pyranosylations employing
easily accessible acetonide-protected donors. A wide variety of alcohol nucleophiles …

Stereospecific furanosylations catalyzed by bis-thiourea hydrogen-bond donors

AB Mayfield, JB Metternich, AH Trotta… - Journal of the …, 2020 - ACS Publications
We report a new method for stereoselective O-furanosylation reactions promoted by a
precisely tailored bis-thiourea hydrogen-bond-donor catalyst. Furanosyl donors outfitted with …

Cooperative Catalysis in Stereoselective O- and N-Glycosylations with Glycosyl Trichloroacetimidates Mediated by Singly Protonated Phenanthrolinium Salt and …

J Ghorai, L Almounajed, S Noori… - Journal of the American …, 2024 - ACS Publications
The development of small-molecule catalysts that can effectively activate both reacting
partners simultaneously represents a pivotal pursuit in advancing the field of stereoselective …

Reaction Rate and Stereoselectivity Enhancement in Glycosidations with O-Glycosyl Trihaloacetimidate Donors due to Catalysis by a Lewis Acid–Nitrile Cooperative …

T Li, T Li, Y Yang, Y Qiu, Y Liu, M Zhang… - The Journal of …, 2024 - ACS Publications
Activation of O-glycosyl trihaloacetimidate glycosyl donors with AuCl3 as a catalyst and
pivalonitrile (t BuCN) as a ligand led to excellent glycosidation results in terms of yield and …

Stereoselective Glycosylation for 1,2-cis-Aminoglycoside Assembly by Cooperative Atom Transfer Catalysis

H Li, D Zhang, C Li, L Yin, Z Jiang… - Journal of the American …, 2024 - ACS Publications
We report here a new catalytic method for exclusively 1, 2-cis-α-selective glycosylation that
assembles a wide variety of 1, 2-cis-aminoglycosidic linkages in complex glycans and …

O-Glycosyl Trichloroacetimidates as Glycosyl Donors and Platinum(IV) Chloride as a Dual Catalyst Permitting Stereo- and Regioselective Glycosidations

T Li, T Li, H Zhuang, F Wang, RR Schmidt… - ACS Catalysis, 2021 - ACS Publications
Stereo-and regioselective glycosidation is still a great challenge in carbohydrate chemistry.
Among the tremendous endeavors in this area, acid–base catalysis, available to O-glycosyl …

Enantioselective Organocopper-Catalyzed Hetero Diels–Alder Reaction through in Situ Oxidation of Ethers into Enol Ethers

A Yesilcimen, NC Jiang, FH Gottlieb… - Journal of the American …, 2022 - ACS Publications
We disclose a catalytic method for the enantio-and diastereoselective union of alkyl ethers
and heterodienes. We demonstrate that a chiral Cu–BOX complex catalyzes the efficient …