152389-00-9Relevant articles and documents
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.
Acid-catalysed Transformation of α-Trifluoromethanesulfonates of γ- and δ-Lactones into 2,5-Disubstituted Homochiral Tetrahydrofurans
Wheatley, Joseph R.,Bichard, Claire J. F.,Mantell, Simon J.,Son, Jong Chan,Hughes, David J.,et al.
, p. 1065 - 1067 (2007/10/02)
Excellent yields of methyl tetrahydrofuran-α-carboxylates are obtained by treatment of 2-O-trifluoromethanesulfonates (triflates) of either 1,4- or 1,5-lactones with acid in methanol; in some cases, very different tetrahydrofurans may result from acid or