A chemoenzymatic synthesis of differentially protected D-talose derivatives
Banwell, Martin; Edwards, Alison; Lambert, John N; Ma, Xinghua; Watson, Keith G
Description
The synthesis of the D-talose derivatives from the readily available and enantiomerically pure cis-1,2-dihydrocatechol was discussed. The synthesis included a stannylene acetal-mediated epimerization process. The dehydroxylation of D-galactal provided a different route to target. The triacetates were chemically correlated with known derivatives of D-talose. A mixture of these compounds was also subjected to reaction with aqueous trifluoroacetic acid to affect global deprotection and generate...[Show more]
dc.contributor.author | Banwell, Martin | |
---|---|---|
dc.contributor.author | Edwards, Alison | |
dc.contributor.author | Lambert, John N | |
dc.contributor.author | Ma, Xinghua | |
dc.contributor.author | Watson, Keith G | |
dc.date.accessioned | 2015-12-13T22:24:57Z | |
dc.date.available | 2015-12-13T22:24:57Z | |
dc.identifier.issn | 0004-9425 | |
dc.identifier.uri | http://hdl.handle.net/1885/73004 | |
dc.description.abstract | The synthesis of the D-talose derivatives from the readily available and enantiomerically pure cis-1,2-dihydrocatechol was discussed. The synthesis included a stannylene acetal-mediated epimerization process. The dehydroxylation of D-galactal provided a different route to target. The triacetates were chemically correlated with known derivatives of D-talose. A mixture of these compounds was also subjected to reaction with aqueous trifluoroacetic acid to affect global deprotection and generate D-talose. | |
dc.publisher | CSIRO Publishing | |
dc.source | Australian Journal of Chemistry | |
dc.subject | Keywords: Catalysts; Chromatographic analysis; Derivatives; Hydrochloric acid; Isomers; Mixtures; Nuclear magnetic resonance; Oxidation; Single crystals; Spectroscopic analysis; Synthesis (chemical); X ray analysis; Enantiometry; Epimerization; Flash chromatography | |
dc.title | A chemoenzymatic synthesis of differentially protected D-talose derivatives | |
dc.type | Journal article | |
local.description.notes | Imported from ARIES | |
local.description.refereed | Yes | |
local.identifier.citationvolume | 55 | |
dc.date.issued | 2002 | |
local.identifier.absfor | 030503 - Organic Chemical Synthesis | |
local.identifier.ariespublication | MigratedxPub3519 | |
local.type.status | Published Version | |
local.contributor.affiliation | Banwell, Martin, College of Physical and Mathematical Sciences, ANU | |
local.contributor.affiliation | Edwards, Alison, College of Physical and Mathematical Sciences, ANU | |
local.contributor.affiliation | Lambert, John N, Monash University | |
local.contributor.affiliation | Ma, Xinghua, College of Physical and Mathematical Sciences, ANU | |
local.contributor.affiliation | Watson, Keith G, Monash University | |
local.bibliographicCitation.issue | 1 & 2 | |
local.bibliographicCitation.startpage | 95 | |
local.bibliographicCitation.lastpage | 103 | |
dc.date.updated | 2015-12-11T08:11:56Z | |
local.identifier.scopusID | 2-s2.0-0036306019 | |
Collections | ANU Research Publications |
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