156928-10-8

Basic information

• Product Name: (3S,3aR,6aS)-Hexahydrofuro[2,3-b]furan-3-ol
• Synonyms: (3S,3aR,6aS)-Hexahydrofuro[2,3-b]furan-3-ol;[3S-(3α,3aβ,6aβ)]-Hexahydrofuro[2,3-b]furan-3-ol
• CAS NO: 156928-10-8
• Molecular Formula: C₆H₁₀O₃
• Molecular Weight: 130.1418
• Product Categories: Chiral Reagents;Heterocycles;Impurities;Intermediates;Chiral Reagents, Heterocycles, Impurities, Intermediates
• Mol File: 156928-10-8.mol
• Article Data: 18

Chemical Properties

• Boiling Point: 251.5±20.0 °C(Predicted)
• Appearance: /
• Density: 1.275±0.06 g/cm3(Predicted)
• Storage Temp.: Hygroscopic, Refrigerator, under inert atmosphere
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 14.07±0.20(Predicted)
• CAS DataBase Reference: (3S,3aR,6aS)-Hexahydrofuro[2,3-b]furan-3-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,3aR,6aS)-Hexahydrofuro[2,3-b]furan-3-ol(156928-10-8)
• EPA Substance Registry System: (3S,3aR,6aS)-Hexahydrofuro[2,3-b]furan-3-ol(156928-10-8)

Safety Data

• Hazardous Substances Data: 156928-10-8(Hazardous Substances Data)

Usage

Uses

An intermediate in the preparation of HIV-1 Protease Inhibitor. An isomeric impurity of Bisfuranol.

Upstream product

• 1191-99-7 2,3-dihydro-2H-furan 
• 23147-58-2 glycolaldehyde dimer 
• 109789-19-7 hexahydrofuro[2,3-b]furan-3-ol 
• 445389-44-6 2,3,3a,6a-tetrahydrofuro[2,3-b]furan-4-one 
• 108-05-4 vinyl acetate 
• 725264-64-2 (3S,3AR,6AS)-hexahydrofuro[2,3-b]furan-3-yl benzoate 
• 809286-93-9 (3aR,6aR)-3a,4,5,6a-tetrahydrofuro[2,3-b]furan-3(2H)-one 
• 73828-22-5 (2S,3R)-3-Allyl-2-Hydroxybernsteinsaeure-diethylester 
• 88481-64-5 (2S,3S)-3-(2-propenyl)-1,2,4-butanetriol 
• 109789-18-6 (2aRS,3aSR)-hexahydrofuro[2,3-b]furan-3-one 
• 109789-17-5 (3aRS,6aSR)-3-methylene-4H-hexahydrofuro<2,3-b>furan 

Downstream Products

• 253265-98-4 Carbonic acid 2,5-dioxo-pyrrolidin-1-yl ester (3S,3aR,6aS)-(hexahydro-furo[2,3-b]furan-3-yl) ester 
• 156879-13-9 L-739-594 
• 854745-99-6 (3R,3aS,6aR) and (3S,3aR,6aS)-hexahydrofuro[2,3-b]furan-3-yl 4-nitrophenyl carbonate 
• 186487-59-2 {(1S,3S,4S)-1-Benzyl-4-[(3S,3aR,6aS)-(hexahydro-furo[2,3-b]furan-3-yl)oxycarbonylamino]-3-hydroxy-5-phenyl-pentyl}-carbamic acid tert-butyl ester 
• 206361-99-1 darunavir 
• 206361-99-1 darunavir 
• 288296-64-0 (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl-4-nitrophenyl carbonate 

Relevant articles and documents

Preparation method of hexahydrofuranofuranol derivative, intermediate and preparation method thereof

The invention relates to the field of medicine synthesis, in particular to a preparation method of a hexahydrofuranofuranol derivative, an intermediate and a preparation method thereof. The preparation method comprises a condensation reaction, a deprotection reaction and a cyclization reaction, wherein R1 and R2 are hydrogen or hydroxyl protecting groups, R3 is alkyl, acyl, ether, ester or aryl, and X is oxygen, sulfur or nitrogen. In the preparation process of the hexahydrofuranofuranol derivative, the compound shown in the formula I is subjected to a condensation reaction, so that the product with very high optical purity can be prepared by adopting the way. The preparation method can be used for commercially producing and preparing the darunavir key intermediate (3R, 3aS, 6aR)- hexahydrofuro-[2, 3-b]-3-ol, and is a very economical route suitable for industrial production.

Synthesis of hexahydro furo [2, 3 - b] furan - 3 - ol and its enantiomer

The invention discloses synthetic methods of hexahydrofuro[2,3-b]furan-3-ol and an enantiomer thereof. The synthetic method of hexahydrofuro[2,3-b]furan-3-ol comprises the step c or the step b to the step c or the step a to the step c in the following synthetic route as shown in the description. The synthetic method of the enantiomer (3R,3aS,6aR)hexahydrofuro[2,3-b]furan-3-ol comprises the step c to the step f or the step b to the step f or the step a to the step f in the following synthetic route as shown in the description, wherein R1 is selected from C1 to C4 alkyl or aralkyl, and R2 is selected from C1 to C4 alkyl. The synthetic methods provided by the invention have the advantages of cheap and easily available raw materials, simple operation, low cost and the like, are suitable for large-scale production, and have practical value for realization of industrialized production of darunavir.

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.