Abstract
A couple of enantiomeric octopyranoses, endowed with differentiated protective groups, namely the L-threo-D-talo-and D-threo-L-talo- octose derivatives L- 6 and D- 6, were synthesized from the enantiomers of threose L- 1 and D- 1 in ca 10% overall yield in five individual steps. The synthetic plan emphasizes the value of 2-(trimethylsiloxy)furan (TMSOF) as four-carbon homologative reactant of homochiral aldehyde precursors en route to higher-carbon monosaccharide units.
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