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Total Synthesis of Tri‐, Hexa‐ and Heptasaccharidic Substructures of the O‐Polysaccharide of Providencia rustigianii O34
Author(s) -
Ahadi Somayeh,
Awan Shahid I.,
Werz Daniel B.
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202000496
Subject(s) - hexa , fucose , chemistry , stereochemistry , polysaccharide , organic chemistry , biochemistry , galactose
A general and efficient strategy for synthesis of tri‐, hexa‐ and heptasaccharidic substructures of the lipopolysaccharide of Providencia rustigianii O34 is described. For the heptasaccharide seven different building blocks were employed. Special features of the structures are an α‐linked galactosamine and the two embedded α‐fucose units, which are either branched at positions‐3 and ‐4 or further linked at their 2‐position. Convergent strategies focused on [4+3], [3+4], and [4+2+1] couplings. Whereas the [4+3] and [3+4] coupling strategies failed the [4+2+1] strategy was successful. As monosaccharidic building blocks trichloroacetimidates and phosphates were employed. Global deprotection of the fully protected structures was achieved by Birch reaction.