dc.contributor.author |
Rodriguez Garcia, E |
en |
dc.contributor.author |
Brimble, Margaret |
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dc.contributor.author |
Vogel, P |
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dc.date.accessioned |
2011-09-21T21:58:00Z |
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dc.date.issued |
2006 |
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dc.identifier.citation |
EUR J ORG CHEM 3845-3855 25 Aug 2006 |
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dc.identifier.issn |
1434-193X |
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dc.identifier.uri |
http://hdl.handle.net/2292/8200 |
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dc.description.abstract |
The cross-aldol condensation of N-benzyl-2,5-dideoxy-2,5-imino-3,4-O-isopropylidene-l-ribose with 4,6-O-benzylidene-2-deoxy-α-d-erythro-hexopyranosid-3-ulose (potassium enolate + HMPA) gave an aldol as the major product. DAST-induced water elimination gave two enones that were converted into the aza-C-disaccharides (+)-4 [methyl 2-deoxy-2-(1,2,5-trideoxy-2,5-imino-l-ribitol-1C-yl)-α-d-glucopyranoside] and (+)-5 (the α-d-allopyranoside analogue). Reduction of the aldol and deprotection provided aza-C-disaccharide (+)-3 {methyl 2-deoxy-2-[(1R or 1S)-2,5-dideoxy-2,5-imino-l-ribitol-1C-yl]-α-d-allopyranoside} with a hydroxymethano linker. |
en |
dc.language |
EN |
en |
dc.publisher |
WILEY-V C H VERLAG GMBH |
en |
dc.relation.ispartofseries |
European Journal of Organic Chemistry |
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dc.rights |
Items in ResearchSpace are protected by copyright, with all rights reserved, unless otherwise indicated. Previously published items are made available in accordance with the copyright policy of the publisher. Details obtained from http://www.sherpa.ac.uk/romeo/issn/1434-193X/ |
en |
dc.rights.uri |
https://researchspace.auckland.ac.nz/docs/uoa-docs/rights.htm |
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dc.subject |
aldol reactions |
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dc.subject |
aza-C-disaccharides |
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dc.subject |
enones |
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dc.subject |
iminoalditols |
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dc.subject |
C-glycosides |
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dc.subject |
hexopyranosid-3-ulose |
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dc.subject |
TYPE-2 DIABETES-MELLITUS |
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dc.subject |
GLYCOSIDASE INHIBITORS |
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dc.subject |
NEURAMINIDASE INHIBITOR |
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dc.subject |
TRIFLUORIDE DAST |
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dc.subject |
INFLUENZA-VIRUS |
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dc.subject |
D-MANNOSE |
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dc.subject |
DIETHYLAMINOSULFUR TRIFLUORIDE |
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dc.subject |
REGIOSELECTIVE DEHYDRATION |
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dc.subject |
N-BUTYLDEOXYNOJIRIMYCIN |
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dc.subject |
TERTIARY ALCOHOLS |
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dc.title |
Synthesis of New Aza-C-disaccharides Linking 4-Deoxy-4-amino-beta-L-erythro-furanose to C-2 of D-Glucose and D-Allose |
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dc.type |
Journal Article |
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dc.identifier.doi |
10.1002/ejoc.200600199 |
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pubs.issue |
17 |
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pubs.begin-page |
3845 |
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pubs.volume |
2006 |
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dc.rights.holder |
Copyright: 2006 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim |
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pubs.end-page |
3855 |
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dc.rights.accessrights |
http://purl.org/eprint/accessRights/RestrictedAccess |
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pubs.subtype |
Article |
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pubs.elements-id |
69529 |
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pubs.org-id |
Science |
en |
pubs.org-id |
Chemistry |
en |
pubs.org-id |
Science Research |
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pubs.org-id |
Maurice Wilkins Centre (2010-2014) |
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pubs.record-created-at-source-date |
2010-09-01 |
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