Chemical synthesis of the rare D-Fuc3NAc containing tetrasaccharide repeating unit of the O-antigenic polysaccharide from E. coli O74

Bera, Anirban; Mukhopadhyay, Balaram

doi:10.1016/j.carres.2021.108366

Cited by 4 publications

(1 citation statement)

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“…[15] However, to maintain the simplicity of the donor molecule, we have used donor 13 for the same. Next, NaOMe mediated de-O-acetylation followed by benzylidene protection at the OÀ 4 and OÀ 6 positions gave the desired acceptor 8 [16] in 75 % yield over two steps (Path II, Scheme 1). In order to get the exclusive formation of the α-glycoside, we thought we can follow the mannose route and invert the 2-position with azido group after glycosylation.…”

Section: Resultsmentioning

confidence: 99%

Chemical Synthesis of the Linker‐Armed Trisaccharide Repeating Unit of the O‐Antigen from Pseudomonas putida BIM B‐1100

2022

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The manuscript reports the concise chemical synthesis of the trisaccharide repeating unit of the O‐antigen from Pseudomonas putida BIM B‐1100 in the form of its aminoethyl glycoside through a linear strategy with rational protecting group manipulations. The challenging aspects of this synthesis include the incorporation of the β‐D‐ManpNAcA and the α‐D‐GlcpNAc residues. The introduction of the desired carboxylic acid moiety has been achieved through late‐stage TEMPO‐mediated oxidation of the primary OH group on the protected trisaccharide. 1,2‐cis aminoethyl glycoside with central glucosamine is used at the reducing end to the leave the scope for further glycoconjugate formation with suitable aglycone without hampering the anomeric stereochemistry.

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Section: Resultsmentioning

confidence: 99%