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Volumn 75, Issue 11, 2010, Pages 3558-3568

Highly Stereoselective de Novo Synthesis of l -Hexoses

Author keywords

[No Author keywords available]

Indexed keywords

DE NOVO SYNTHESIS; DIASTEREO-SELECTIVITY; DIHYDROXYLATION REACTION; DOMINO REACTIONS; DOUBLE BONDS; EPIMERS; ERYTHRO; FUNCTIONALIZATIONS; ISOPROPYLIDENE; STEREO-SELECTIVE; STEREOGENIC CENTERS; SYNTHETIC ROUTES;

EID: 77953007988     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo100077k     Document Type: Article
Times cited : (32)

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    • contrast to previous results reported on similar substrates, no traces of the corresponding gulose isomer was herein detected
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    • 4); however, only C6 O -deacetylation occurred, even after prolonged reaction times
    • 4); however, only C6 O -deacetylation occurred, even after prolonged reaction times.
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    • note
    • Solvent substitution (acetone in place of THF) associated with a low temperature (0 °C) was necessary to partially deactivate the reagent, with the aim to prevent formation of 32. Stronger reduction conditions yielded 32 in high yield (see Experimental Section for details).
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    • note
    • It should be mentioned that very prolonged times were required to complete ring opening of 29, as the C3 position was greatly hindered by both the C4 benzyl group and the C1-C6 bridge.


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