152389-00-9

Upstream product

• 67-56-1 methanol 
• 152388-99-3 3-O-benzyl-5,6-O-isopropylidene-2-O-trifluoromethylsulfonyl-D-glucono-1,4-lactone 
• 485812-47-3 3-O-benzyl-5,6-O-isopropylidene-D-glucono-1,4-lactone 
• 485812-46-2 3-O-benzyl-D-glucono-1,4-lactone 
• 65877-63-6 3-O-benzyl-D-glucopyranose 
• 156944-02-4 Trifluoro-methanesulfonic acid (3R,4S,5R)-4-benzyloxy-5-((R)-1-benzyloxy-2-hydroxy-ethyl)-2-oxo-tetrahydro-furan-3-yl ester 

Downstream Products

• 485812-67-7 isopropyl 2,5-anhydro-D-mannonate 
• 485812-50-8 methyl 2,5-anhydro-3-O-benzyl-6-deoxy-D-mannonate 
• 485812-49-5 methyl 2,5-anhydro-3-O-benzyl-6-deoxy-6-iodo-D-mannonate 
• 485812-68-8 isopropyl 2,5-anhydro-6-O-p-tolylsulfonyl-D-mannonate 
• 485812-48-4 methyl 2,5-anhydro-3-O-benzyl-6-O-p-tolylsulfonyl-D-mannonate 

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.

Tetrahydropyran Derivatives from γ- and δ-Hexonolactones

Both δ- and γ-hexonolactones provide templates for the construction of bicyclic lactones in which a new tetrahydropyran ring has been formed from overall elimination of water from the C-2 and C-6 hydroxyl groups.Such studies may provide a strategy for the syntheis of C-glycosides from elimination of water between C-2 and C-6 of heptonolactones.

Acid-catalysed Transformation of α-Trifluoromethanesulfonates of γ- and δ-Lactones into 2,5-Disubstituted Homochiral Tetrahydrofurans

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