Complex tetrahydrofurans from carbohydrate lactones: THF amino acids as building blocks for unnatural biopolymers
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 suita...
| Main Authors: | , , , , , , |
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| Format: | Journal article |
| Language: | English |
| Published: |
2002
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| _version_ | 1826259025836113920 |
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| author | Long, D Smith, M Martin, A Wheatley, JR Watkin, D Muller, M Fleet, G |
| author_facet | Long, D Smith, M Martin, A Wheatley, JR Watkin, D Muller, M Fleet, G |
| author_sort | Long, D |
| collection | OXFORD |
| description | 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. |
| first_indexed | 2024-03-06T18:43:21Z |
| format | Journal article |
| id | oxford-uuid:0da953a5-90bf-4082-a8b7-fed4ed75bc58 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-06T18:43:21Z |
| publishDate | 2002 |
| record_format | dspace |
| spelling | oxford-uuid:0da953a5-90bf-4082-a8b7-fed4ed75bc582022-03-26T09:41:43ZComplex tetrahydrofurans from carbohydrate lactones: THF amino acids as building blocks for unnatural biopolymersJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:0da953a5-90bf-4082-a8b7-fed4ed75bc58EnglishSymplectic Elements at Oxford2002Long, DSmith, MMartin, AWheatley, JRWatkin, DMuller, MFleet, GThe 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. |
| spellingShingle | Long, D Smith, M Martin, A Wheatley, JR Watkin, D Muller, M Fleet, G Complex tetrahydrofurans from carbohydrate lactones: THF amino acids as building blocks for unnatural biopolymers |
| title | Complex tetrahydrofurans from carbohydrate lactones: THF amino acids as building blocks for unnatural biopolymers |
| title_full | Complex tetrahydrofurans from carbohydrate lactones: THF amino acids as building blocks for unnatural biopolymers |
| title_fullStr | Complex tetrahydrofurans from carbohydrate lactones: THF amino acids as building blocks for unnatural biopolymers |
| title_full_unstemmed | Complex tetrahydrofurans from carbohydrate lactones: THF amino acids as building blocks for unnatural biopolymers |
| title_short | Complex tetrahydrofurans from carbohydrate lactones: THF amino acids as building blocks for unnatural biopolymers |
| title_sort | complex tetrahydrofurans from carbohydrate lactones thf amino acids as building blocks for unnatural biopolymers |
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