192725-55-6

Basic information

• Product Name: (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl 4-nitrophenyl carbonate
• Synonyms: Carbonic acid (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl 4-nitrophenyl ester
• CAS NO: 192725-55-6
• Molecular Formula: C13H13NO7
• Molecular Weight: 295.249
• Mol File: 192725-55-6.mol

Chemical Properties

• CAS DataBase Reference: (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl 4-nitrophenyl carbonate(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl 4-nitrophenyl carbonate(192725-55-6)
• EPA Substance Registry System: (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl 4-nitrophenyl carbonate(192725-55-6)

Safety Data

• Hazardous Substances Data: 192725-55-6(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl 4-nitrophenyl carbonate is used as a building block in organic synthesis for the creation of more complex organic molecules. Its unique structure and specific stereochemistry make it a valuable component in the synthesis of various organic compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl 4-nitrophenyl carbonate may be utilized as a key intermediate in the development of new drugs. Its unique structure and properties can be leveraged to design and synthesize novel pharmaceutical compounds with potential therapeutic applications.
Used in Chemical Research:
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl 4-nitrophenyl carbonate is also used in chemical research to study its properties and explore its potential uses. Researchers in the field of organic chemistry can investigate the compound's reactivity, stability, and other characteristics to gain insights into its behavior and possible applications in various chemical processes.

Upstream product

• 7693-46-1 4-Nitrophenyl chloroformate 
• 156928-09-5 (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol 
• 5070-13-3 bis-(p-nitrophenyl) carbonate 
• 162119-35-9 3-acetoxy-(3R,3αS,6αR)-bis-tetrahydrofuran 
• 109789-19-7 (3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol 
• 109789-18-6 (2aRS,3aSR)-hexahydrofuro[2,3-b]furan-3-one 
• 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 
• 178557-39-6 ethyl 2-[(3aR,5S,6R,6aR)-5-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-yl]acetate 
• 58399-68-1 (3aS,4S,6aR)-2-Oxo-hexahydro-furo[3,4-b]furan-4-carbaldehyde 
• 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 
• 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 
• 1008743-57-4 3-deoxy-3-(2-ethoxy-2-oxoethyl)-1,2-O-isopropylidene-α-D-ribo-pentodialdo-1,4-furanose 
• 80923-96-2 ((3aR,4S,6aR)-2-oxohexahydrofuro[3,4-b]furan-4-yl)methyl benzoate 
• 58399-67-0 (3aR,4S,6aR)-4-(hydroxymethyl)tetrahydrofuro[3,4-b]furan-2(3H)-one 

Downstream Products

• 186487-62-7 {(1S,3S,4S)-1-Benzyl-4-[(3R,3aS,6aR)-(hexahydro-furo[2,3-b]furan-3-yl)oxycarbonylamino]-3-hydroxy-5-phenyl-pentyl}-carbamic acid tert-butyl ester 
• 681028-76-2 ((1S,2R)-3-Azido-1-benzyl-2-hydroxy-propyl)-carbamic acid (3R,3aS,6aR)-(hexahydro-furo[2,3-b]furan-3-yl) ester 
• 288296-75-3 (3R,3aS,6aR)hexahydrofuro[2,3-b]furan-3-yl N-(1S,2R)-3-[(1,3-benzodioxol-5-ylsulfonyl)(5-cyano-2,2-dimethylpentyl)amino]-1-benzyl-2-hydroxypropylcarbamate 
• 252873-24-8 ((1S,2R)-1-Benzyl-3-cyclohexyloxyamino-2-hydroxy-propyl)-carbamic acid (3R,3aS,6aR)-(hexahydro-furo[2,3-b]furan-3-yl) ester 
• 313679-55-9 (3R,3AS,6AR)-hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-3-[(1,3-benzodioxol-5-ylsulfonyl)(isobutyl)amino]-1-[4-(benzyloxy)benzyl]-2-hydroxypropylcarbamate 

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.

PROCESS FOR THE PREPARATION OF SULFONAMIDES USEFUL AS RETROVIRAL PROTEASE INHIBITORS

The present invention relates to a process for the preparation of sulfonamides useful as retroviral protease inhibitors.

Substrate envelope-designed potent HIV-1 protease inhibitors to avoid drug resistance

Summary The rapid evolution of HIV under selective drug pressure has led to multidrug resistant (MDR) strains that evade standard therapies. We designed highly potent HIV-1 protease inhibitors (PIs) using the substrate envelope model, which confines inhib

Research and development of an efficient synthesis of hexahydrofuro[2,3-b] furan-3-ol moiety - a key component of the HIV protease inhibitor candidates

A highly efficient method for synthesizing racemic hexahydrofuro[2,3-b] furan-3-ol has been developed utilizing a lanthanide catalyst, such as Yh(fod)3, to promote condensation of 23-dihydrofuran and glycolaldehyde dimer. Access to either optically enriched enantiomer of bisfuran alcohol can be obtained by using this method employing chiral ligands with the lanthanide catalyst In support of Gilead Sciences' protease inhibitor project, this method has been demonstrated to be a robust and scalable process with potential application for the construction of a variety of furo[2,3-b]furan derivatives.

PROCESS FOR PREPARATION OF HIV PROTEASE INHIBITORS

A process for the synthesis of bisfuran intermediates useful for preparing antiviral HIV protease inhibitor compounds is hereby disclosed.

Novel P1 chain-extended HIV protease inhibitors possessing potent anti-HIV activity and remarkable inverse antiviral resistance profiles

A novel series of tyrosine-derived HIV protease inhibitors was synthesized and evaluated for in vitro antiviral activity against wild-type virus and two protease inhibitor-resistant viruses. All of the compounds had wild-type antiviral activities that were similar to or greater than several currently marketed HIV protease inhibitors. In addition, a number of compounds in this series were more potent against the drug-resistant mutant viruses than they were against wild-type virus.

Novel arylsulfonamides possessing sub-picomolar HIV protease activities and potent anti-HIV activity against wild-type and drug-resistant viral strains

A novel series of P1′ chain-extended arylsufonamides was synthesiszed and evaluated for wild-type HIV protease inhibitory activity and in vitro antiviral activity against wild type virus and two protease inhibitor-resistant mutant viruses. All of the comp

Retroviral protease inhibiting compounds

A compound comprising a substituent of the formula (II) is disclosed as an HIV protease inhibitor. Intermediates for making such compounds and processes for making such intermediates are also disclosed.

Evaluation of furofuran as a P2 ligand for symmetry-based HIV protease inhibitors

The hexahydrofurofuranyloxy group was evaluated as a conformationally constrained P2 ligand for symmetry-based HIV protease inhibitors. A number of compounds showed nM level activity against HIV in MT4 cells and lower protein binding than the licensed protease inhibitor ritonavir. However, replacement of 5-thiazole of ritonavir with a furofuran caused a reduction of the bioavailability in vivo.