Block Synthesis of Tetra- and Hexasaccharides (β-d-Glycero-d-manno-Hepp-(1→4)-[α-l-Rhap-(1→3)-β-d-glycero-d-manno-Hepp-(1→4)]n-α-l-Rhap-OMe (n = 1 and 2)) Corresponding to Multiple Repeat Units of the Glycan from the Surface-Layer Glycoprotein from Bacillus thermoaerophilus
- 27 August 2008
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 73 (18) , 7003-7010
- https://doi.org/10.1021/jo801414c
Abstract
A fully stereocontrolled block synthesis of the title tetra- and hexasaccharides has been achieved taking advantage of the ability of the 4,6-O-benzylidene acetal to control the stereochemistry of the β-d-glycero-d-mannoheptopyranoside unit and of a 2,3-O-diphenylmethylene acetal to install the α-l-rhamnopyranosidic linkages. Comparison of the spectral data for the hexasaccharide with that of the natural isolate confirms the structure of this very unusual and structurally challenging glycan.Keywords
This publication has 47 references indexed in Scilit:
- Stereocontrolled Synthesis of the d- and l-glycero-β-d-manno-Heptopyranosides and Their 6-Deoxy Analogues. Synthesis of Methyl α-l-Rhamno-pyranosyl-(1→3)-d-glycero-β-d-manno-heptopyranosyl- (1→3)-6-deoxy-glycero-β-d-manno-heptopyranosyl-(1→4)-α-l- rhamno-pyranoside, a Tetrasaccharide Subunit of the Lipopolysaccharide from Plesimonas shigelloidesJournal of the American Chemical Society, 2006
- Improved Synthesis of 1‐Benzenesulfinyl Piperidine and Analogs for the Activation of Thioglycosides in Conjunction with Trifluoromethanesulfonic Anhydride*Journal of Carbohydrate Chemistry, 2005
- Synthesis of Anemoclemoside B, the First Natural Product with an Open-Chain Cyclic Acetal Glycosidic LinkageOrganic Letters, 2005
- 1-Benzenesulfinyl Piperidine/Trifluoromethanesulfonic Anhydride: A Potent Combination of Shelf-Stable Reagents for the Low-Temperature Conversion of Thioglycosides to Glycosyl Triflates and for the Formation of Diverse Glycosidic LinkagesJournal of the American Chemical Society, 2001
- Recent advances in the construction of β-D-mannose and β-D-mannosamine linkagesJournal of the Chemical Society, Perkin Transactions 1, 2000
- Direct chemical synthesis of β-mannopyranosides and other glycosides via glycosyl triflatesTetrahedron, 1998
- Are Glycosyl Triflates Intermediates in the Sulfoxide Glycosylation Method? A Chemical and 1H, 13C, and 19F NMR Spectroscopic InvestigationJournal of the American Chemical Society, 1997
- Direct Synthesis of β-Mannopyranosides by the Sulfoxide MethodThe Journal of Organic Chemistry, 1997
- Glycan structure of a heptose-containing S-layer glycoprotein of Bacillus thermoaerophillusGlycobiology, 1996
- Glycan structure of a heptose-containing S-layer glycoprotein of Bacillus thermoaerophilusGlycobiology, 1995