ArticleThe Journal of organic chemistry2014
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.
Article in The Journal of organic chemistry, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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5 citing papers in PubMed, 14 citations in OpenAlex.
- Stereoselective Synthesis of β-d-Manno-heptopyranoside via CsThe Journal of organic chemistry · 2022Article
- A Lead-Based Fragment Library Screening of the Glycosyltransferase WaaG fromPharmaceuticals (Basel, Switzerland) · 2022Article
- Straight Forward and Versatile Differentiation of the l-Frontiers in chemistry · 2020Article
- Synthesis of 3-Monatshefte fur chemie · 2017Article
- Large-Scale Synthesis of Crystalline 1,2,3,4,6,7-Hexa-European journal of organic chemistry · 2015Article
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3 authors at 1 institution in 1 country.
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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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