Convergent synthesis of 4-O-phosphorylated L-glycero-D-manno-heptosyl lipopolysaccharide core oligosaccharides based on regioselective cleavage of a 6,7-O-tetraisopropyldisiloxane-1,3-diyl protecting group

The Journal of Organic Chemistry
Christian StanettyPaul Kosma

Abstract

The structurally conserved lipopolysaccharide core region of many Gram-negative bacteria is composed of trisaccharides containing 4-O-phosphorylated L-glycero-D-manno-heptose (L,D-Hep) units, which act as ligands for antibodies and lectins. The disaccharides Glc-(1→3)-Hep4P Hep-(1→3)-Hep4P and Hep-(1→7)-Hep4P and the branched trisaccharide Glc-(1→3)-[Hep-(1→7)]-Hep4P, respectively, have been synthesized from a methyl heptopyranoside acceptor in less than 10 steps. The synthetic strategy was based on the early introduction of a phosphotriester at position 4 of heptose followed by a regioselective opening of a 6,7-O-(1,1,3,3-tetraisopropyl-1,3-disiloxane-1,3-diyl) group allowing for a straightforward access to glycosylation at position 7. Perbenzylated N-phenyl trifluoroacetimidate glucosyl and heptosyl derivatives served as α-selective glycosyl donors.

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Citations

Aug 26, 2016·Journal of Colloid and Interface Science·Mangesh KokateAnand Gole
Jun 23, 2015·European Journal of Organic Chemistry·Christian Stanetty, Ian R Baxendale
Jun 16, 2016·Chemistry : a European Journal·Abdellatif TikadStéphane P Vincent
Aug 28, 2020·Frontiers in Chemistry·Christoph SusterChristian Stanetty
Nov 26, 2020·The Journal of Organic Chemistry·Kwok-Kong Tony MongLi-Ching Shen

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Methods Mentioned

BETA
glycosylation
glucosylation
NMR
column chromatography

Software Mentioned

TREAT

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