Straightforward Synthesis of the Pentasaccharide Repeating Unit of the O -Antigenic Polysaccharide from the Enteropathogenic Escherichia coli O142

The pentasaccharide repeating unit rich in 2-acetamidosugars corresponding to the O-antigenic polysaccharide from entero-pathogenic Escherichia coli (E. coli) has been synthesized as the p-me-thoxyphenyl glycoside in excellent yield using a sequential glycosylationstrategy. Regioselective glycosylat...

Full description

Saved in:
Bibliographic Details
Published inSynthesis (Stuttgart) Vol. 55; no. 5; pp. 773 - 778
Main Authors Jana, Swapan Kumar, Shit, Pradip, Misra, Anup Kumar
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.03.2023
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
carbohydrates
synthesis
HCLO4-SIO2
DIARRHEA
E
oligosaccharides
coli
ACETAL
glycosylation
CATALYST
glycosides
HIGHLY EFFICIENT
REMOVAL
INFECTION
DERIVATIVES
Online AccessGet more information

Cover

More Information
Summary:The pentasaccharide repeating unit rich in 2-acetamidosugars corresponding to the O-antigenic polysaccharide from entero-pathogenic Escherichia coli (E. coli) has been synthesized as the p-me-thoxyphenyl glycoside in excellent yield using a sequential glycosylationstrategy. Regioselective glycosylation, use of a single monosaccharideintermediate in multiple glycosylations, and use of thioglycosides asglycosyl donors in the presence of a combination of N-iodosuccinimide(NIS) and perchloric acid supported over silica (HClO4-SiO2) are keycomponents of the synthetic strategy. All glycosylation reactions werehigh-yielding with excellent stereochemical outcome.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0041-1738428