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Control of phosphoryl migratory transesterifications allows regioselecive access to sugar phosphates.

Abstract:
Phosphate esters in polyhydroxylated systems are normally blighted by uncontrolled migration under a variety of reaction conditions. Cesium fluoride is demonstrated as a reagent to control migration of primary phosphates during transesterifications. This allows easy exchange of phosphoryl protecting groups enabling enhanced synthetic strategic flexibility and regioselective phosphate installation. Mechanistic analysis suggests that a fluoride-induced extended solvent sphere modulates steric bulk at phosphorus to favor the primary position.
Publication status:
Published
Peer review status:
Peer Reviewed
Version:
Submitted Manuscript

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Publisher copy:
10.1021/ol303271z

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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
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Funding agency for:
Davis, BG
International AIDS Vaccine Initiative More from this funder
Journal:
Organic Letters
Volume:
15
Issue:
2
Pages:
346-349
Publication date:
2013-01-03
DOI:
EISSN:
1523-7052
ISSN:
1523-7060
URN:
uuid:65b4d86f-7372-4783-910c-62ad4b71089b
Source identifiers:
374214
Local pid:
pubs:374214

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