485812-46-2

Upstream product

• 65877-63-6 3-O-benzyl-D-glucopyranose 

Downstream Products

• 485812-47-3 3-O-benzyl-5,6-O-isopropylidene-D-glucono-1,4-lactone 
• 485812-53-1 methyl 2,5-anhydro-3-O-benzyl-6-O-p-tolylsulfonyl-D-gluconate 
• 485812-48-4 methyl 2,5-anhydro-3-O-benzyl-6-O-p-tolylsulfonyl-D-mannonate 
• 485812-66-6 isopropyl 2,5-anhydro-6-O-p-tolylsulfonyl-D-gluconate 
• 485812-68-8 isopropyl 2,5-anhydro-6-O-p-tolylsulfonyl-D-mannonate 
• 485812-52-0 3-O-benzyl-5,6-O-isopropylidene-D-mannono-1,4-lactone 
• 485812-49-5 methyl 2,5-anhydro-3-O-benzyl-6-deoxy-6-iodo-D-mannonate 
• 485812-54-2 methyl 2,5-anhydro-3-O-benzyl-6-deoxy-6-iodo-D-gluconate 
• 485812-50-8 methyl 2,5-anhydro-3-O-benzyl-6-deoxy-D-mannonate 
• 485812-55-3 methyl 2,5-anhydro-3-O-benzyl-6-deoxy-D-gluconate 
• 485812-67-7 isopropyl 2,5-anhydro-D-mannonate 
• 485812-65-5 isopropyl 2,5-anhydro-D-gluconate 
• 216451-62-6 methyl 2,5-anhydro-6-O-p-tolylsulfonyl-D-gluconate 
• 152388-99-3 3-O-benzyl-5,6-O-isopropylidene-2-O-trifluoromethylsulfonyl-D-glucono-1,4-lactone 

Relevant academic research and scientific papers

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 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.