A Suzuki-Miyaura coupling mediated deprotection as key to the synthesis of a fully lipidated malarial GPI disaccharide.
Ligandless palladium-catalyzed Suzuki-Miyaura coupling converted an inert p-bromobenzyl ether to a DDQ-labile p-(3,4-dimethoxyphenyl) benzyl ether in the presence of azide functionality and this strategy serves as a key step for the convergent synthesis of a fully lipidated malaria GPI disaccharide.
Laboratorium fur Organische Chemie, ETH Zurich, 8093 Zurich, Switzerland. seeberger@org.chem.ethz.ch
Xinyu
X
Liu
Peter H
PH
Seeberger
D000818:Animals; D001593:Benzyl Compounds / Q000737:chemistry; D001969:Bromobenzenes / Q000737:chemistry / Q000378:metabolism; D002384:Catalysis; D004187:Disaccharides / Q000138:chemical synthesis / Q000737:chemistry; D004987:Ethers / Q000737:chemistry / Q000378:metabolism; D017261:Glycosylphosphatidylinositols / Q000138:chemical synthesis / Q000737:chemistry; D008024:Ligands; D008055:Lipids / Q000737:chemistry; D017780:Malaria Vaccines / Q000138:chemical synthesis* / Q000737:chemistry; D010165:Palladium / Q000737:chemistry; D010647:Phenyl Ethers / Q000737:chemistry; D010961:Plasmodium / Q000276:immunology
D001593:Benzyl Compounds; D001969:Bromobenzenes; D004187:Disaccharides; D004987:Ethers; D017261:Glycosylphosphatidylinositols; D008024:Ligands; D008055:Lipids; D017780:Malaria Vaccines; D010647:Phenyl Ethers; D010165:Palladium