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Alkoxyallene‐Based De Novo Synthesis of Rare Deoxy Sugars: New Routes to L ‐Cymarose, L ‐Sarmentose, L ‐Diginose and L ‐Oleandrose
Author(s) -
Brasholz Malte,
Reißig HansUlrich
Publication year - 2009
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200900450
Subject(s) - chemistry , glycosyl donor , monosaccharide , glycosylation , stereochemistry , allene , glycosyl , catalysis , organic chemistry , biochemistry
Starting from lithiated methoxyallene and lactaldehyde derivatives, the four rare 2,6‐dideoxy‐hexoses L ‐cymarose, L ‐sarmentose, L ‐diginose and L ‐oleandrose were synthesized in a stereodivergent fashion. Key steps towards these four target monosaccharides were the oxidative ring openings of allene‐derived 2,5‐dihydrofurans, diastereoselective carbonyl reductions as well as face‐selective hydrogenation protocols. First glycosylation reactions employing thiophenyl glycosyl donors of L ‐cymarose and L ‐diginose were performed in high yields and with fair to excellent stereocontrol. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)