TY - CHAP
T1 - Synthesis and Characterization of 4-Methylphenyl 2,3,4,6-Tetra-O-Benzoyl-1-Thio-β-D-Galactopyranoside
AU - Panza, M.
AU - Mannino, M. P.
AU - Demchenko, Alexei
AU - Baryal, K. N.
N1 - DOI link for Carbohydrate Chemistry Carbohydrate Chemistry book Proven Synthetic Methods, Volume 5 DOI link for Carbohydrate Chemistry Carbohydrate Chemistry book Proven Synthetic Methods, Volume 5 By Paul Kosma, Tanja Wrodnigg, Arnold Stütz
PY - 2021
Y1 - 2021
N2 - 4-Methylphenyl 2,3,4,6-tetra-O-benzoyl-1-thio-ß-d-galactopyranoside has become a common glycosyl donor for the synthesis of various oligosaccharides. Hioglycoside 4, first reported by Kochetkov and coworkers in 1987, is included in a library of glycosyl donors database for the development of programmable one-pot oligosaccharide synthesis. Presented herein is the synthesis and characterization of benzoylated thioglycoside 4 from commercially available d-galactose pentaacetate 1. Intermediate 2 can be obtained directly from d-galactose by copper(II) triflate-catalyzed two-step conversion. Reactions were performed using commercial reagents and solvents and monitored by TLC on Kieselgel 60 F254. 1,2,3,4,6-Penta-O-acetyl-ß-d-galactopyranose was purchased from Carbosynth. Compounds were detected by UV light and by charring with 10% sulfuric acid in methanol.
AB - 4-Methylphenyl 2,3,4,6-tetra-O-benzoyl-1-thio-ß-d-galactopyranoside has become a common glycosyl donor for the synthesis of various oligosaccharides. Hioglycoside 4, first reported by Kochetkov and coworkers in 1987, is included in a library of glycosyl donors database for the development of programmable one-pot oligosaccharide synthesis. Presented herein is the synthesis and characterization of benzoylated thioglycoside 4 from commercially available d-galactose pentaacetate 1. Intermediate 2 can be obtained directly from d-galactose by copper(II) triflate-catalyzed two-step conversion. Reactions were performed using commercial reagents and solvents and monitored by TLC on Kieselgel 60 F254. 1,2,3,4,6-Penta-O-acetyl-ß-d-galactopyranose was purchased from Carbosynth. Compounds were detected by UV light and by charring with 10% sulfuric acid in methanol.
UR - https://www.taylorfrancis.com/books/edit/10.1201/9781351256087/carbohydrate-chemistry-paul-kosma-tanja-wrodnigg-arnold-st%C3%BCtz
M3 - Chapter
BT - Carbohydrate Chemistry
ER -