80923-96-2

Basic information

• Product Name: ((3aR,4S,6aR)-2-oxohexahydrofuro[3,4-b]furan-4-yl)methyl benzoate
• Synonyms: ((3aR,4S,6aR)-2-oxohexahydrofuro[3,4-b]furan-4-yl)methyl benzoate
• CAS NO: 80923-96-2
• Molecular Weight: 262.262
• Mol File: 80923-96-2.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: ((3aR,4S,6aR)-2-oxohexahydrofuro[3,4-b]furan-4-yl)methyl benzoate(CAS DataBase Reference)
• NIST Chemistry Reference: ((3aR,4S,6aR)-2-oxohexahydrofuro[3,4-b]furan-4-yl)methyl benzoate(80923-96-2)
• EPA Substance Registry System: ((3aR,4S,6aR)-2-oxohexahydrofuro[3,4-b]furan-4-yl)methyl benzoate(80923-96-2)

Safety Data

• Hazardous Substances Data: 80923-96-2(Hazardous Substances Data)

Upstream product

• 6612-91-5 ((3aR,5R,65,6aR)-6-hydroxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate 
• 20031-21-4 1,2-O-isopropylidene-α-D-xylose 
• 492-62-6 alpha-D-glucopyranose 
• 6698-46-0 5-O-benzoyl-1,2-O-isopropylidene-α-D-ribofuranos-3-ulose 
• 98-88-4 benzoyl chloride 
• 1008743-57-4 3-deoxy-3-(2-ethoxy-2-oxoethyl)-1,2-O-isopropylidene-α-D-ribo-pentodialdo-1,4-furanose 
• 950583-17-2 (Z)-ethyl 2-((3aR,5S,6aR)-5-((R)-1,2-dihydroxyethyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ylidene)acetate 
• 57466-98-5 (Z)-ethyl 2-((3aR,5S,6aR)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethylfuro[2,3-d][1,3]dioxol-6(3aH,5H,6aH)-ylidene)acetate 
• 2847-00-9 1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose 
• 178557-39-6 ethyl 2-[(3aR,5S,6R,6aR)-5-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-yl]acetate 
• 59256-86-9 ethyl 2-((3aR,5S,6R,6aR)-5-((R)-1,2-dihydroxyethyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-yl)acetate 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 

Downstream Products

• 253265-97-3 1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione 
• 156928-09-5 (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol 
• 192725-55-6 (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl-(4-nitrophenyl)carbonic acid 
• 866594-60-7 (3aS,4S,6aR)-4-methoxy-tetrahydro-furo[3.4-b]furan-2(3H)-one 

Relevant articles and documents

The Chiron Approach to (3 R,3 aS,6 aR)-Hexahydrofuro[2,3- b]furan-3-ol, a Key Subunit of HIV-1 Protease Inhibitor Drug, Darunavir

We describe an enantioselective synthesis of (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol which is a key subunit of darunavir, a widely used HIV-1 protease inhibitor drug for the treatment of HIV/AIDS patients. The synthesis was achieved in optically pure form utilizing commercially available sugar derivatives as the starting material. The key steps involve a highly stereoselective substrate-controlled hydrogenation, a Lewis acid catalyzed anomeric reduction of a 1,2-O-isopropylidene-protected glycofuranoside, and a Baeyer-Villiger oxidation of a tetrahydrofuranyl-2-aldehyde derivative. This optically active ligand alcohol was converted to darunavir efficiently.