725264-69-7

Basic information

• Product Name: (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl benzoate
• Synonyms: (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl benzoate
• CAS NO: 725264-69-7
• Molecular Weight: 234.252
• Mol File: 725264-69-7.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl benzoate(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl benzoate(725264-69-7)
• EPA Substance Registry System: (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl benzoate(725264-69-7)

Safety Data

• Hazardous Substances Data: 725264-69-7(Hazardous Substances Data)

Upstream product

• 252873-50-0 (3S,3aS,6aR)-3-hydroxyhexahydrofuro[2,3-b]furan 
• 156928-09-5 (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol 
• 65-85-0 benzoic acid 
• 98-88-4 benzoyl chloride 
• 809286-93-9 (3aR,6aR)-3a,4,5,6a-tetrahydrofuro[2,3-b]furan-3(2H)-one 

Downstream Products

• 156928-09-5 (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol 

Relevant articles and documents

Catalytic asymmetric synthesis of hexahydro-furofuran-3-ol and its pyran derivatives

The catalytic asymmetric synthesis of hexahydro-furofuran-3-ol, a key fragment of HIV protease inhibitors, is reported. A signature event is represented by the sequential metal catalysis that combines the Pd-catalyzed asymmetric hydroalkoxylation of ene-alkoxyallene and ring-closing metathesis (RCM). Notably, this unprecedented and highly chemoselective approach allows for a unified access to pyranofuranol and furopyranol derivatives.

The efficient synthesis of (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol and its isomers

The stereoselective synthesis of all the possible stereoisomers of bis-tetrahydrofyran alcohol, a ligand used for obtaining HIV protease inhibitors including Darunavir 1 and Brecanavir 2 has been achieved. A key intermediate 4-pentenal 5 was obtained by employing a Wittig olefination-Claisen rearrangement protocol from d-glyceraldehyde derivative 3 as a source of chirality. The 4-pentenal was readily converted in the bis-THF alcohol moiety in three steps.

Production method of hexahydrofurofuranol derivative, intermediate therefor and production method thereof

The present invention provides a method for producing compound (XIV) useful as an intermediate for pharmaceutical agents efficiently and economically on an industrial scale without using ozone oxidation and highly toxic reagent, and an intermediate used for this method. Particularly, the present invention provides a method for producing a compound having an absolute configuration represented by the formula (XV) and an enantiomer thereof without using a technique such as optical resolution and the like, and an intermediate used for this method. (1) Compound (XIII) as a starting material is led to compound (I), and after introducing a protecting group, subjected to reduction and cyclization to give compound (XIV). Particularly, compound (XIII) as a material is led to compound (I) via compound (XX) to produce compound (XIV). Using an optically active compound (XIII) as a starting material, a compound having an absolute configuration represented by the formula (XV) and the like are produced highly stereoselectively. (2) Compound (XXI) as a starting material is stereoselectively reduced to give compound (XXII), and by introduction of a protecting group, reduction and cyclization, compound (XXVI) is obtained, and by inverting hydroxyl group, compound (XV) is produced. wherein each symbol is as defined in the specification.