Carbon-branched δ-tetrahydrofuran sugar amino acids (SAAs) as dipeptide isostere scaffolds

Carbon-branched δ-tetrahydrofuran sugar amino acids (SAAs) as dipeptide isostere scaffolds

The synthesis of the first branched sugar amino acid (SAA) scaffolds [methyl (3 R,4 R,5 R)-5-azidomethyl-3,4-dihydroxy-tetrahydrofuran-3-carboxylate and methyl (3 R,4 R,5 S)-5-azidomethyl-3,4-dihydroxy-tetrahydrofuran-3-carboxylate] by an efficient intramolecular displacement of a highly hindered ne...

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Bibliographic Details
Published in:Tetrahedron: asymmetry Vol. 19; no. 24; pp. 2887 - 2894
Main Authors: Simone, Michela I., Edwards, Alison A., Tranter, George E., Fleet, George W.J.
Format: Journal Article
Language:English
Published: Elsevier Ltd 12-12-2008
Online Access:Get full text
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Summary:The synthesis of the first branched sugar amino acid (SAA) scaffolds [methyl (3 R,4 R,5 R)-5-azidomethyl-3,4-dihydroxy-tetrahydrofuran-3-carboxylate and methyl (3 R,4 R,5 S)-5-azidomethyl-3,4-dihydroxy-tetrahydrofuran-3-carboxylate] by an efficient intramolecular displacement of a highly hindered neopentyl triflate allows access to enantiopure THF derivatives which have carbon substituents.
ISSN:0957-4166
1362-511X
DOI:10.1016/j.tetasy.2008.12.012