jo0620258_si_004.cif (16.72 kB)
Total Syntheses of Conformationally Locked Difluorinated Pentopyranose Analogues and a Pentopyranosyl Phosphate Mimetic
dataset
posted on 2007-03-02, 00:00 authored by Jonathan A. L. Miles, Lisa Mitchell, Jonathan M. Percy, Kuldip Singh, E. UneyamaTrifluoroethanol has been elaborated, via a telescoped sequence involving a metalated difluoroenol, a
difluoroallylic alcohol, [2,3]-Wittig rearrangement, and ultimately an RCM reaction and requiring minimal
intermediate purification, to a number of cyclooctenone intermediates. Epoxidation of these intermediates
followed by transannular ring opening or dihydroxylation, then transannular hemiacetalization delivers
novel bicyclic analogues of pentopyranoses, which were elaborated (in one case) to an analogue of a
glycosyl phosphate.
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sequenceTotal Synthesesnovel bicyclic analoguesRCM reactionPentopyranosyl Phosphate MimeticTrifluoroethanolmetalated difluoroenolDifluorinated Pentopyranose AnaloguespentopyranoseWittigtransannular ring openingEpoxidationConformationallyglycosyl phosphatedihydroxylationdifluoroallylic alcoholtransannular hemiacetalizationpurificationcyclooctenone intermediatesrearrangement
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