2004
Carbohydrates
U 0500
A Suzuki—Miyaura Coupling Mediated Deprotection as Key to the Synthesis of
Fully Lipidated Malarial GPI Disaccharide. — The first synthesis of a fully lipi50- 163 adated
malarial GPI disaccharide (VIII) based on a new protecting group strategy
involving 4-bromobenzyl ethers is reported. This chemically stable group is converted
to a DDQ-labile 4-(3,4-dimethoxyphenyl)benzyl ether using a ligandless
Suzuki—Miyaura coupling reaction. The reactivity of such 4-(hetero-substituted phenyl) benzyl ethers as protection for hydroxyl groups can be tuned by the substitution
patterns on the aryl ring and should find further application in organic synthesis of complex molecules. — (LIU, X.; SEEBERGER*, P. H.; Chem. Commun. (Cambridge)
2004, 15, 1708-1709; Lab. Org. Chem., ETH-Hoenggerberg, CH-8093 Zuerich,
Switz.; Eng.) — M. Paetzel
2004