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
• Article Data: 9

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

General Description

The chemical compound "(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl 4-nitrophenyl carbonate" is an organic compound consisting of a furofuran ring with a 4-nitrophenyl carbonate group attached. The compound has a six-membered ring with a furan structure and a carbonate group attached to a 4-nitrophenyl group. It has a specific stereochemistry denoted by the (3R,3aS,6aR) configuration. (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl 4-nitrophenyl carbonate may have potential applications in organic synthesis or as a building block for more complex organic molecules. Its properties and potential uses may be further studied and explored in the field of organic chemistry.

Upstream product

• 7693-46-1 4-Nitrophenyl chloroformate 
• 156928-09-5 (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol 
• 109789-19-7 (3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol 
• 109789-18-6 (2aRS,3aSR)-hexahydrofuro[2,3-b]furan-3-one 
• 5070-13-3 bis-(p-nitrophenyl) carbonate 
• 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 
• 162119-35-9 3-acetoxy-(3R,3αS,6αR)-bis-tetrahydrofuran 

Downstream Products

• 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 
• 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 
• 635728-49-3 [14C]-Darunavir ethanolate 
• 1263998-29-3 (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl [(1S,2R)-3-[[(4-aminophenyl)sulfonyl](2-methylpropyl)-d2-amino]-2-hydroxy-1-(phenylmethyl)propyl]-d1-carbamate trifluoroacetate 
• 1169870-25-0 C₂₇H₃₇N₃O₆S 
• 288296-33-3 {(1S,2R)-3-[(Benzo[1,3]dioxole-5-sulfonyl)-(4-dibenzylamino-2,2-dimethyl-butyl)-amino]-1-benzyl-2-hydroxy-propyl}-carbamic acid (3R,3aS,6aR)-(hexahydro-furo[2,3-b]furan-3-yl) ester 

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.

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

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.