252873-01-1

Basic information

• Product Name: BIS THF Nitro Derivative 2
• Synonyms: BIS THF Nitro Derivative 2;(3S,3aS,6aR)-Hexahydrofuro[2,3-b]furan-3-yl 4-Nitrophenyl Ester Carbonic Acid;ULTSJNOQNKVDBM-QJPTWQEYSA-N
• CAS NO: 252873-01-1
• Molecular Formula: C13H13NO7
• Molecular Weight: 295.24482
• Mol File: 252873-01-1.mol

Chemical Properties

• Boiling Point: 461.3±45.0 °C(Predicted)
• Appearance: /
• Density: 1.45±0.1 g/cm3(Predicted)
• CAS DataBase Reference: BIS THF Nitro Derivative 2(CAS DataBase Reference)
• NIST Chemistry Reference: BIS THF Nitro Derivative 2(252873-01-1)
• EPA Substance Registry System: BIS THF Nitro Derivative 2(252873-01-1)

Safety Data

• Hazardous Substances Data: 252873-01-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
BIS THF Nitro Derivative 2 is used as an impurity in the development of [HIV-aspartyl protease inhibitors] for [their potential role in the treatment of HIV/AIDS]. The presence of this derivative in the synthesis process of these inhibitors may affect the overall efficacy and safety of the final drug product.
Used in Research and Development:
BIS THF Nitro Derivative 2 serves as a subject of study in the field of medicinal chemistry and drug development. Researchers investigate the properties, interactions, and potential effects of this compound on the overall performance of HIV-aspartyl protease inhibitors to improve their design and synthesis.
Used in Quality Control and Analysis:
In the manufacturing process of HIV-aspartyl protease inhibitors, BIS THF Nitro Derivative 2 is used as a reference compound for quality control and analytical purposes. Its identification and quantification in the final product help ensure the purity, safety, and efficacy of the antiretroviral drugs.

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 
• 605654-10-2 {[1S,2R]-2-hydroxy-1-(4-hydroxy-benzyl)-3-[N-isobutyl-(N-4-methoxybenzenesulfonyl)-amino]-propyl}-carbamic acid hexahydro-[3R,3aS,6aR]-furo[2,3-b]furan-3-yl ester 
• 622866-42-6 {(1S,2R)-[1-(4-formyl-benzyl)]-(2R)-2-hydroxy-3-[N-isobutyl-(N-4-methoxy-benzenesulfonyl)-amino]-propyl}-carbamic acid [3R,3aS,6aR]-hexahydrofuro[2,3-b]furan-3-yl ester 
• 622866-41-5 trifluoromethanesulfonic acid 4-(2S,3R)-{2-([2R,3S]-hexahydro-furo[2,3-b]furan-(3R)-3-yloxycarbonylamino)-3-hydroxy-4-[N-isobutyl-(N-methoxybenzenesulfonyl)-amino]-butyl}-phenyl ester 
• 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 

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.

Crystalline Darunavir

The present invention relates to a non-solvated crystalline Darunavir, process for its preparation and pharmaceutical composition comprising it. The present invention also relates to a process for the preparation of amorphous Darunavir from a non-solvated crystalline Darunavir.

CRYSTALLINE DARUNAVIR

The present invention relates to a non-solvated crystalline Darunavir, process for its preparation and pharmaceutical composition comprising it. The present invention also relates to a process for the preparation of amorphous Darunavir from a non-solvated crystalline Darunavir.

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

HIV protease inhibiting compounds

A compound of the formula is disclosed as an HIV protease inhibitor. Methods and compositions for inhibiting an HIV infection are also disclosed.

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.

HIV protease inhibiting compounds

A compound of the formula is disclosed as an HIV protease inhibitor. Methods and compositions for inhibiting an HIV infection are also 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.