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Volumn 44, Issue 38, 2005, Pages 6227-6231

Synthesis of enantiopure carbohydrate mimetics by Lewis acid catalyzed rearrangement of 1,3-dioxolanyl-substituted 1,2-oxazines

Author keywords

Carbohydrates; Heterocycles; Rearrangement; Reduction

Indexed keywords

BIOMIMETIC MATERIALS; CATALYSIS; ORGANIC ACIDS; REDUCTION; SUBSTITUTION REACTIONS;

EID: 25844449046     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200501127     Document Type: Article
Times cited : (85)

References (61)
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    • [5] The rapid fragmentation of the residue R seems to be quite important for the smooth cyclization to compounds 4-7. With the 4-methoxy-substituted analogue of syn-3 similar reactions were observed but owing to the persistence of the methyl group the outcome was more complicated. Details will be presented in a future publication.
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    • The constitution and configuration of products presented herein were confirmed by 2D NMR spectra, associated with NOE-studies; X-ray crystallographic analyses of key compounds 23, 33, and 35 as well as of the precursor of the ring-opened product 27 are available. Details will be presented in a future full publication.
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    • In this case the hydride reagent attacks the bicyclic compound 13 from the other face; in contrast to 6,9, or 11, there is no shielding alkyl group. The configuration was undoubtedly proven by X-ray crystallographic analysis at the stage of 23.
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    • for the use of sugar diaminocarboxylic acids, see: F. Sicherl, V. Wittmann, Angew. Chem. 2005, 117, 2133-2136;
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.