Iron(iii) chloride-catalyzed activation of glycosyl chlorides.

Org Biomol Chem

Department of Chemistry and Biochemistry, University of Missouri - St Louis, One University Boulevard, St Louis, Missouri 63121, USA.

Published: December 2018

AI Article Synopsis

  • Glycosyl chlorides typically require harsh conditions and toxic promoters for activation, which can be a drawback in chemical processes.
  • Recent research by the Ye and Jacobsen groups demonstrated the possibility of activating these compounds under milder organocatalytic conditions, but challenges like slow reactions and moderate yields persisted.
  • This study presents a more straightforward method using inexpensive ferric chloride (FeCl3) as a catalyst, showing promising preliminary results in activating various glycosyl chlorides effectively.

Article Abstract

Glycosyl chlorides have historically been activated using harsh conditions and/or toxic stoichiometric promoters. More recently, the Ye and the Jacobsen groups showed that glycosyl chlorides can be activated under organocatalytic conditions. However, those reactions are slow, require specialized catalysts and high temperatures, but still provide only moderate yields. Presented herein is a simple method for the activation of glycosyl chlorides using abundant and inexpensive ferric chloride in catalytic amounts. Our preliminary results indicate that both benzylated and benzoylated glycosyl chlorides can be activated with 20 mol% of FeCl3.

Download full-text PDF

Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6541213PMC
http://dx.doi.org/10.1039/c8ob02413hDOI Listing

Publication Analysis

Top Keywords

glycosyl chlorides
20
activation glycosyl
8
chlorides activated
8
glycosyl
5
chlorides
5
ironiii chloride-catalyzed
4
chloride-catalyzed activation
4
chlorides glycosyl
4
chlorides historically
4
historically activated
4

Similar Publications

-GalNAc glycans on glycoproteins with eight different core structures sharing a common α-glycosidic linkage (-GalNAc-α-Ser/Thr) are critical in various physiological and pathological processes. Among the eight -GalNAc glycan cores, core 2 characterized by a GlcNAcβ1-6(Galβ1-3)GalNAc structural motif plays a significant role in regulating diverse biological processes, such as immune response modulation, adhesive properties of selectins, and gastrointestinal tract protection. However, the large-quantity synthesis of core 2 containing glyco-amino acids for downstream solid-phase peptide synthesis is challenging.

View Article and Find Full Text PDF

Practical synthesis of -aryl glycosides redox-neutral Borono-Catellani reaction.

Chem Commun (Camb)

January 2025

Sauvage Center for Molecular Sciences, Engineering Research Center of Organosilicon Compounds & Materials (Ministry of Education), Hubei Key Lab on Organic and Polymeric OptoElectronic Materials, College of Chemistry and Molecular Sciences and The Institute for Advanced Studies and TaiKang Center for Life and Medical Sciences, Wuhan University, 430072, Wuhan, China.

Herein, we describe a practical Borono-Catellani strategy for the efficient synthesis of -aryl glycosides, with readily available arylboronic esters and glycosyl chlorides as the building blocks. It features mild reaction conditions, excellent diastereoselectivities, and good functional group tolerance. A diverse array of highly decorated -(hetero)aryl glycosides are obtained in a convergent and redox-neutral manner.

View Article and Find Full Text PDF

Introduction: Milan hypertensive strain (MHS) of rat represents as one of the ideal rat models to study the genetic form of hypertension associated with aberrant renal salt reabsorption. In contrast to Milan normotensive strain (MNS), MHS rats possess missense mutations in three adducin genes and develop hypertension at 3 months old due to upregulation of sodium-chloride cotransporter (NCC). At pre-hypertensive stage (23-25 days old), MHS rats show enhanced protein abundance of Na+-K+-2Cl- cotransporter (NKCC2) but retain blood pressure comparable to MNS probably through enhanced GFR and reduced NCC and α-subunit of epithelial sodium channel (α-ENaC) expressed in distal convoluted tubule (DCT) and collecting duct (CD).

View Article and Find Full Text PDF

Ferric Chloride Promoted Glycosidation of Alkyl Thioglycosides.

Molecules

October 2024

Department of Chemistry, Saint Louis University, 3501 Laclede Ave., St. Louis, MO 63103, USA.

Reported herein is a new reaction for glycosylation with thioglycosides in the presence of iron(III) chloride. Previously, FeCl was used for the activation of thioglycosides as a Lewis acid co-promoter paired with NIS. In the reported process, although 5.

View Article and Find Full Text PDF

Mutations in the CLCNKB gene (1p36), encoding the basolateral chloride channel ClC-Kb, cause type 3 Bartter syndrome. We identified a family with a mixed Bartter/Gitelman phenotype and early-onset kidney failure and by employing a candidate gene approach, identified what we believe is a novel homozygous mutation (CLCNKB c.499G>T [p.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!