216451-62-6Relevant academic research and scientific papers
Synthesis of oligomers of tetrahydrofuran amino acids: Furanose carbopeptoids
Smith, Martin D.,Long, Daniel D.,Marquess, Daniel G.,Claridge, Timothy D.W.,Fleet, George W.J.
, p. 2039 - 2040 (1998)
An acid catalysed ring rearrangement of a triflate derivative of D-mannono-γ-lactone 6 is the key step in the synthesis of the C-glycosyl sugar amino acid derivatives 3 and 4, examples of carbohydrate amino acid building blocks with specific conformational preferences suitable for incorporation into combinatorial amide libraries; homo-oligomerisation via solution phase coupling procedures affords furanose carbopeptoids 1 which adopt novel solution state secondary structures.
Complex tetrahydrofurans from carbohydrate lactones: THF amino acids as building blocks for unnatural biopolymers
Long, Daniel D.,Smith, Martin D.,Martin, Angeles,Wheatley, Joseph R.,Watkin, David G.,Mueller, Mattaius,Fleet, George W. J.
, p. 1982 - 1998 (2007/10/03)
The multi-gram syntheses of two epimeric six-carbon tetrahydrofurancarboxylates based upon a D-arabinofuranose template are described. An approach to 3-O-benzyl protected derivatives is also detailed. Introduction of nitrogen at C-6 of these scaffolds leads to the generation of building blocks suitable for the generation of oligomers which possess well defined secondary structures. Radical bromination facilitates introduction of nitrogen at C-2, to afford anomeric α-amino acid derivatives which are elaborated to two unnatural diastereomers of the potent herbicidal natural product hydantocidin. X-Ray crystal structures of N-methyl-2-azido-2-deoxy-α-D-arabino-hex-2-ulofuranosonamide and N-dodecyl-2-azido-2-deoxy-β-D-arabino-hex-2-ulofuranosonamide are also disclosed.
