252873-50-0

Basic information

• Product Name: (3S,3aS,6aR)-Hexahydrofuro[2,3-b]furan-3-ol
• Synonyms: (3S,3aS,6aR)-Hexahydrofuro[2,3-b]furan-3-ol
• CAS NO: 252873-50-0
• Molecular Formula: C₆H₁₀O₃
• Molecular Weight: 130.1418
• Product Categories: Chiral Reagents;Heterocycles;Impurities;Intermediates;Chiral Reagents, Heterocycles, Impurities, Intermediates
• Mol File: 252873-50-0.mol
• Article Data: 5

Chemical Properties

• Melting Point: 67 °C
• Boiling Point: 251.5±20.0 °C(Predicted)
• Appearance: /
• Density: 1.275±0.06 g/cm3(Predicted)
• PKA: 14.07±0.20(Predicted)
• CAS DataBase Reference: (3S,3aS,6aR)-Hexahydrofuro[2,3-b]furan-3-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,3aS,6aR)-Hexahydrofuro[2,3-b]furan-3-ol(252873-50-0)
• EPA Substance Registry System: (3S,3aS,6aR)-Hexahydrofuro[2,3-b]furan-3-ol(252873-50-0)

Safety Data

• Hazardous Substances Data: 252873-50-0(Hazardous Substances Data)

Upstream product

• 1191-99-7 2,3-dihydro-2H-furan 
• 23147-58-2 glycolaldehyde dimer 
• 809286-93-9 (3aR,6aR)-3a,4,5,6a-tetrahydrofuro[2,3-b]furan-3(2H)-one 
• 72157-18-7 4-trimethylsilyloxy-n-butyraldehyde 
• 102191-92-4 tert-butyldimethylsiloxyacetaldehyde 
• 1015081-32-9 C₁₇H₃₄O₅Si 
• 1015081-28-3 (2R,3S)-1,5-di-(tert-butyldimethylsilyl)-3-formylpentane-1,2,5-triol 

Downstream Products

• 725264-69-7 (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl benzoate 
• 206361-99-1 darunavir 
• 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 
• 206361-99-1 darunavir 
• 799241-85-3 Carbonic acid 2,5-dioxo-pyrrolidin-1-yl ester (3S,3aS,6aR)-(hexahydro-furo[2,3-b]furan-3-yl) ester 
• 186488-54-0 (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl 4-nitrophenyl carbonate 

Relevant articles and documents

METHOD FOR PRODUCING HEXAHYDROFUROFURANOL DERIVATIVE

The invention provides a method for producing efficiently and inexpensively on an industrial scale compound (VII) having a desired diastereomer ratio and enantiomer excess, intermediates useful in this method, and methods for producing the intermediates; and a method for producing compound (VIII), which is obtained from compound (I) and compound (II) by the route showing below.

Efficient synthesis of 3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol from glycolaldehyde

A one-step diastereoselective (up to 98:2) synthesis of the bis-furan alcohol of Darunavir and other HIV drug candidates has been achieved utilizing the novel cyclizatlon of glycolaldehyde and 2,3-dihydrofuran. The cycloaddition was catalyzed by a variety of catalysts including those formed from tin(II) triflate and common chiral ligands such as BINAP and Evans's box ligands. An efficient and unique enzymatic process enhanced the enantiomeric purity to provide the target in optically pure form.

METHOD FOR PRODUCING HEXAHYDROFUROFURANOL DERIVATIVE

Disclosed is a method for producing a compound (IV) which comprises a step for obtaining a compound (III) by reacting a compound (I) with a compound (II) in the presence of an optionally substituted cyclic secondary amine, and a step for obtaining the compound (IV) by removing R1 and R2 from the compound (III) sequentially or at a time and then cyclizing the compound from which the R1 and R2 are removed. Also disclosed is a method for producing a high-purity compound (IV), an intermediate thereof, and a method for producing the intermediate.