Work

Novel 2,3-unsaturated O-glycosides containing an alkynyl function in their aglycones

Year: 2024

Type: article

Abstract: This paper describes the synthesis of seven D-glucosides, 3a-g, and six D-galactosides, 4a-f, all containing an alkynyl function in their aglycones. The reaction was performed using dichloromethane as solvent in the presence of Montmorillonite K-10. The structure of all compounds were confirmed employing IR, 1 H NMR and 13 C NMR spectroscopic techniques. The aim was to study their conformational energies using ab initio Hartree Fock method with 6-31G as basis set. Two compounds, namely, ( R )-(+)-3-butyn-2-yl 4,6-di- O -acetyl-2,3-dideoxy-α-D- erythro -hex-2-enopyranoside, 3d, and ( R )-(+)-3-butyn-2-yl 4,6-di- O -acetyl-2,3-dideoxy-α-D- threo -hex-2-enopyranoside, 4d, were subjected to X-ray diffraction analyses and their experimental values compared with the calculated values obtained by molecular orbital calculations. Our studies have found a good correlation between the two types of glycosides.

Source: Results in Chemistry

DOI: 10.1016/j.rechem.2024.101991

Authors: Adriana C.N. de Melo, Natália M. Bezerra, Rajendra M. Srivastava, Carlos Alberto de Simone

Institutions: Universidade Federal de Pernambuco, Universidade de São Paulo, Instituto de Física de São Carlos, Universidade Federal de Alagoas

Language: English

Topic: Carbohydrate Chemistry and Synthesis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: gold

Estimated APC paid: $1,490

Funders: Coordenação de Aperfeiçoamento de Pessoal de Nível Superior, Ministerio de Educación, Cultura y Deporte, Fundação de Amparo à Ciência e Tecnologia do Estado de Pernambuco