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

Abstract:
The synthesis of the first branched sugar amino acid (SAA) scaffolds [methyl (3R,4R,5R)-5-azidomethyl-3,4-dihydroxy-tetrahydrofuran-3-carboxylate and methyl (3R,4R,5S)-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. © 2008 Elsevier Ltd. All rights reserved.
Publication status:
Published

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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Role:
Author
Journal:
TETRAHEDRON-ASYMMETRY
Volume:
19
Issue:
24
Pages:
2887-2894
Publication date:
2008-12-12
DOI:
EISSN:
1362-511X
ISSN:
0957-4166
URN:
uuid:b681bf9b-b468-45b2-a911-a6a5bae0e3c9
Source identifiers:
41108
Local pid:
pubs:41108
Language:
English

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