Stereoselective Synthesis of 2,3-Unsaturated Pseudoglycosides Promoted by Ultrasound

Juliana L. L. F. Regueira; Claudio R. Dantas; Jucleiton J. R. de Freitas; Anderson J. F. Santos da Silva; João R. Freitas Filho; Paulo H. Menezes; Juliano C. R. Freitas

doi:10.1055/s-0035-1561344

Synthesis, Table of Contents

Synthesis 2016; 48(07): 1069-1078
DOI: 10.1055/s-0035-1561344

paper

Stereoselective Synthesis of 2,3-Unsaturated Pseudoglycosides Promoted by Ultrasound

Authors

Juliana L. L. F. Regueira

^aDepartamento de Química, Universidade Federal Rural de Pernambuco, Recife, 50740-560 PE, Brazil
Claudio R. Dantas

^aDepartamento de Química, Universidade Federal Rural de Pernambuco, Recife, 50740-560 PE, Brazil
Jucleiton J. R. de Freitas

^bDepartamento de Química Fundamental, Universidade Federal de Pernambuco, Recife, 52171-900 PE, Brazil
Anderson J. F. Santos da Silva

^aDepartamento de Química, Universidade Federal Rural de Pernambuco, Recife, 50740-560 PE, Brazil
João R. Freitas Filho

^aDepartamento de Química, Universidade Federal Rural de Pernambuco, Recife, 50740-560 PE, Brazil
Paulo H. Menezes

^bDepartamento de Química Fundamental, Universidade Federal de Pernambuco, Recife, 52171-900 PE, Brazil
Juliano C. R. Freitas*

^aDepartamento de Química, Universidade Federal Rural de Pernambuco, Recife, 50740-560 PE, Brazil

^cCentro de Educação e Saúde, Universidade Federal de Campina Grande, Olho D’agua da Bica, s/n, Cuité, 58175-000 PB, Brazil Email: julianocrufino@yahoo.com.br

Abstract

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Abstract

The ultrasound-promoted glycosidation of several alcohols using 3,4,6-tri-O-acetyl-d-glucal as the glycosyl donor is described. The products were obtained in a short reaction time at room temperature in good yield and α-selectivity in an open flask, thus avoiding the preparation and manipulation of unstable or sensitive catalysts.

Key words

2,3-unsaturated O-glycosides - glycosidation reaction - ultrasound - p-toluenesulfonic acid - 3,4,6-tri-O-acetyl-d-glucal

Full Text

References

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Supplementary Material

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