Inverse-electron demand Diels Alder Reactions between glycals and tetrazines.

Cycloaddition Reaction Electrons Heterocyclic Compounds Sugars
Glycal HOMO-[LUMO + 1] gaps IEDDA cycloaddition Pyridazine Tetrazine

Journal

Carbohydrate research
ISSN: 1873-426X
Titre abrégé: Carbohydr Res
Pays: Netherlands
ID NLM: 0043535

Informations de publication

Date de publication:
Sep 2022
Historique:
received: 26 02 2022
revised: 09 06 2022
accepted: 13 06 2022
pubmed: 24 6 2022
medline: 10 8 2022
entrez: 23 6 2022
Statut: ppublish

Résumé

The inverse-electron demand Diels Alder reaction (IEDDA) of substituted tetrazines with 2,3-unsaturated sugars (glycals) has been investigated to prepare novel carbohydrate-based heterocycles. The cycloaddition reactions occurred in moderate to good, isolated yields and gave acyclic, C-linked pyranose diazines as the major products (33-90%). The effects of variations in sugars, sugar protecting groups, and reaction solvents on the yields and products obtained in these reactions were studied. Lower yields of adducts were isolated for TBDMS-protected glucals and for 4,6-O-benzylidene protected glucals. When unprotected sugars were used, the reactions failed to give the desired cycloadducts. A range of substituted tetrazines were also evaluated in these reactions. For comparison, HOMO-[LUMO + 1] gaps for glycal-tetrazine pairs were calculated using Density Functional (DFT) calculations at the B3LYP/631G+ level.

Identifiants

DOI: 10.1016/j.carres.2022.108623 PMID: 35738050
pubmed: 35738050
pii: S0008-6215(22)00124-0
doi: 10.1016/j.carres.2022.108623
pii:
doi:

Substances chimiques

Heterocyclic Compounds 0
Sugars 0

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

IM

Pagination

108623

Informations de copyright

Copyright © 2022 Elsevier Ltd. All rights reserved.

Auteurs

Cecilia H Marzabadi (CH)

Department of Chemistry and Biochemistry, Seton Hall University, 400 South Orange Ave., South Orange, NJ, 07079, USA. Electronic address: cecilia.marzabadi@shu.edu.

Stephen P Kelty (SP)

Department of Chemistry and Biochemistry, Seton Hall University, 400 South Orange Ave., South Orange, NJ, 07079, USA; Center for Computational Research, Seton Hall University, South Orange, NJ, 07079, USA.

Alexandra Altamura (A)

Department of Chemistry and Biochemistry, Seton Hall University, 400 South Orange Ave., South Orange, NJ, 07079, USA; Hackensack Meridian Medical School, 340 Kingsland St, Nutley, NJ, 07110, USA.

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Classifications MeSH

questionsmedicales.fr › Technologie, industrie et agriculture › Technologie › Technologie pharmaceutique › Techniques de chimie synthétique › Réaction de cycloaddition › Inverse-electron demand Diels Alder Reactions...
questionsmedicales.fr › Phénomènes physiques › Phénomènes magnétiques › Phénomènes électromagnétiques › Électrons › Inverse-electron demand Diels Alder Reactions...
questionsmedicales.fr › Composés hétérocycliques › Inverse-electron demand Diels Alder Reactions...
questionsmedicales.fr › Glucides › Sucres › Inverse-electron demand Diels Alder Reactions...