Polyfluoroglycoside Synthesis via Simple Alkylation of an Anomeric Hydroxyl Group: Access to Fluoroetoposide Analogues.


Journal

The Journal of organic chemistry
ISSN: 1520-6904
Titre abrégé: J Org Chem
Pays: United States
ID NLM: 2985193R

Informations de publication

Date de publication:
19 03 2021
Historique:
pubmed: 26 2 2021
medline: 3 7 2021
entrez: 25 2 2021
Statut: ppublish

Résumé

In this work, we have developed a new approach for the synthesis of fluoroglycoside analogues. This strategy used a simple alkylation protocol and allowed the installation of a simple aglyconic alkane with the β configuration. Moreover, the glycosylation of fluorinated glucoside analogues with 4'-demethylepipodophyllotoxin furnished novel fluoroetoposide analogues. In these cases, the α anomers were formed as major products with an

Identifiants

pubmed: 33630592
doi: 10.1021/acs.joc.0c02841
doi:

Substances chimiques

Glucosides 0

Types de publication

Journal Article Research Support, Non-U.S. Gov't

Langues

eng

Sous-ensembles de citation

IM

Pagination

4812-4824

Auteurs

Thomas Tremblay (T)

Département de Chimie, Université Laval, PROTEO, 1045 av. De la Médecine, Québec City, QC, Canada G1 V 0A6.

Jacob St-Gelais (J)

Département de Chimie, Université Laval, PROTEO, 1045 av. De la Médecine, Québec City, QC, Canada G1 V 0A6.

Maxime Houde (M)

Département de Chimie, Université Laval, PROTEO, 1045 av. De la Médecine, Québec City, QC, Canada G1 V 0A6.

Denis Giguère (D)

Département de Chimie, Université Laval, PROTEO, 1045 av. De la Médecine, Québec City, QC, Canada G1 V 0A6.

Articles similaires

Benzhydryl Compounds Humans Glucosides Heart Failure Malaysia
Protein Processing, Post-Translational Humans Blood Coagulation Fibrin Fibrinogen
Protein Processing, Post-Translational Humans Acetylglucosamine Animals Neoplasms
Diabetic Retinopathy Animals Humans Signal Transduction Protein Serine-Threonine Kinases

Classifications MeSH