Glycosyl oxazolines serve as active donors for iterative synthesis of type I oligosaccharides

Synthesis of Galβ1 → 3GlcNAc-repeating saccharides is limited mainly by the formation of less-reactive oxazolines. We herein report an expeditious approach that requires trichloroacetyloxazolines as reactive glycosyl donors. Using only two disaccharide building blocks, the iterative oxazoline format...

Full description

Saved in:
Bibliographic Details
Published inChemical communications (Cambridge, England) Vol. 6; no. 84; pp. 12173 - 12176
Main Authors Verma, Nitish, Tu, Zhijay, Renata, Septila, Lin, Chun-Hung
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 17.10.2024
Royal Society of Chemistry
Subjects
Carbohydrates
Chemistry
Chemistry, Multidisciplinary
Disaccharides
Oligosaccharides
Physical Sciences
Science & Technology
Synthesis
MANNAN-BINDING PROTEIN
CHAIN
LIGANDS
LACTOSYLCERAMIDES
Online AccessGet full text

Cover

More Information
Summary:Synthesis of Galβ1 → 3GlcNAc-repeating saccharides is limited mainly by the formation of less-reactive oxazolines. We herein report an expeditious approach that requires trichloroacetyloxazolines as reactive glycosyl donors. Using only two disaccharide building blocks, the iterative oxazoline formation and glycosylation synthesized hexa- and octasaccharides with overall yields of 47% and 26% in four and six steps, respectively. Oxazoline-based iterative glycosylation to synthesize hexa- and octasaccharides in an expeditious manner.
Bibliography:11
generated oxazoline
14
15
synthesis of hexasaccharide oxazoline
Electronic supplementary information (ESI) available: Synthesis of oxazolines
https://doi.org/10.1039/d4cc03247k
in situ
glycosylation of oxazoline donors with cyclohexanol with different promoters, glycosylation of
2b
2
5
and
and NMR spectra of new compounds. See DOI
by coupling of
9
improved synthesis of hexasaccharide
with acceptor
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 14
content type line 23
ISSN:1359-7345
1364-548X
1364-548X
DOI:10.1039/d4cc03247k