Synthesis and Characterization of Propargyl 2,3,4,6-Tetra-O-Acetyl-β-d-Glucopyranoside
2021
Viktors Kumpiņš, Jevgeņija Lugiņina, D. Imperio, Māris Turks

The propargyl function in organic synthesis in general and in carbohydrate chemistry in particular is a well-established dipolarophile component in 1,3-dipolar cycloaddition reaction for the synthesis of different triazole or isoxazole derivatives. Another useful application of propargyl glucopyranoside has been reported in a one-pot three-component reaction of alkyne-aldehyde-aniline for the successful construction of quinoline-based glycoconjugates. The chapter describes a more detailed protocol for the synthesis of 2,3,4,6-tetra-O-acetyl-ß-d-glucopyranoside 2 than that described, from 1,2,3,4,6-penta-O-acetyl-ß-d-glucopyranose 1 and propargyl alcohol in the presence of boron trifluoride etherate. The reaction was performed using commercial reagents and solvents purified prior to use according to standard procedures. Reactions were monitored by TLC.


Keywords
Propargyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
DOI
10.1201/9781351256087
Hyperlink
https://www.taylorfrancis.com/chapters/edit/10.1201/9781351256087-19/synthesis-characterization-propargyl-2-3-4-6-tetra-acetyl-glucopyranoside-kumpin%C5%A1-luginina-turks-imperio

Kumpiņš, V., Lugiņina, J., Imperio, D., Turks, M. Synthesis and Characterization of Propargyl 2,3,4,6-Tetra-O-Acetyl-β-d-Glucopyranoside. In: Carbohydrate Chemistry: Proven Synthetic Methods. Vol.5. P.Kosma, A.Stutz, T.Wrodnigg ed. Boca Raton, London, New York: CRC Press, 2021. pp.147-151. e-ISBN 9781351256087. Available from: doi:10.1201/9781351256087

Publication language
English (en)
The Scientific Library of the Riga Technical University.
E-mail: uzzinas@rtu.lv; Phone: +371 28399196