Glycerol carbonate in Ferrier reaction: Access to new enantiopure building blocks to develop glycoglycerolipid analogues.
Glycerol carbonate and tri-O-acetyl-D-glucal were used for the synthesis of glycero-functionalized carbohydrates. Ferrier reaction between the two partners afforded the O-glucoside in 84% yield. Spontaneous crystallization yielded 28% of a pure diastereoisomer with the S configuration as determined by X-ray crystallography. Then, the azido-glycerosugar was prepared in two steps: ring opening of the cyclic carbonate with sodium azide and per-acetylation with an excellent yield of 94%. A library of glycoconjugates were prepared using a 1,3-dipolar cycloaddition in yields ranging from 64 to 99%.
Laboratório de Síntese de Compostos Bioativos, Universidade Federal Rural de Pernambuco, Dois Irmãos, 52171-900, Brazil; Université d'Orléans et CNRS, ICOA, UMR 7311, BP 6759, F-45067 Orléans, France.
Pollyanna Leite Ferreira
PL
da Costa
Laboratório de Síntese de Compostos Bioativos, Universidade Federal Rural de Pernambuco, Dois Irmãos, 52171-900, Brazil; Departamento de Química Fundamental, Universidade Federal de Pernambuco, 50.740-540, Recife, PE, Brazil.
Valentina Nascimento
VN
Melo
Laboratório de Síntese de Compostos Bioativos, Universidade Federal Rural de Pernambuco, Dois Irmãos, 52171-900, Brazil.
Bruna Martins
BM
Guimarães
Université d'Orléans et CNRS, ICOA, UMR 7311, BP 6759, F-45067 Orléans, France.
Marie
M
Schuler
UMR CNRS 6283, Faculté des Sciences et Techniques, Université du Maine, Avenue Olivier Messiaen, 72085 Le Mans Cedex 9, France.
Vanessa
V
Pimenta
Université d'Orléans et CNRS, ICOA, UMR 7311, BP 6759, F-45067 Orléans, France.
Patrick
P
Rollin
Université d'Orléans et CNRS, ICOA, UMR 7311, BP 6759, F-45067 Orléans, France. Electronic address: arnaud.tatibouet@univ-orleans.fr.
Arnaud
A
Tatibouët
Laboratório de Síntese de Compostos Bioativos, Universidade Federal Rural de Pernambuco, Dois Irmãos, 52171-900, Brazil. Electronic address: ronaldo.noliveira@ufrpe.br.
Ronaldo Nascimento
RN
de Oliveira
D002254:Carbonates / Q000737:chemistry*; D018360:Crystallography, X-Ray; D005990:Glycerol / Q000737:chemistry*; D006001:Glycoconjugates / Q000737:chemistry*; D006017:Glycolipids / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure
D002254:Carbonates; D006001:Glycoconjugates; D006017:Glycolipids; C015903:glycerolglycolipids; D005990:Glycerol
1,2,3-Triazole; Click chemistry; Glycerol carbonate; Tri-O-acetyl-D-glucal