96086-02-1

Basic information

• Product Name: 2(5H)-Furanone, 5-[(benzoyloxy)methyl]-, (S)-
• CAS NO: 96086-02-1
• Molecular Formula: C12H10O4
• Molecular Weight: 218.209
• Mol File: 96086-02-1.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 2(5H)-Furanone, 5-[(benzoyloxy)methyl]-, (S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2(5H)-Furanone, 5-[(benzoyloxy)methyl]-, (S)-(96086-02-1)
• EPA Substance Registry System: 2(5H)-Furanone, 5-[(benzoyloxy)methyl]-, (S)-(96086-02-1)

Safety Data

• Hazardous Substances Data: 96086-02-1(Hazardous Substances Data)

Upstream product

• 81703-94-8 methyl (2Z)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]acrylate 
• 15397-14-5 C₂₆H₂₀O₈ 
• 140160-60-7 C₂₆H₂₀O₈ 
• 78508-96-0 (5S)-5-(hydroxymethyl)-5H-furan-2-one 
• 98-88-4 benzoyl chloride 

Downstream Products

• 131347-68-7 2',3'-Dideoxy-2',3'-α-methano-α-cytidine 
• 131267-41-9 Benzoic acid (1S,2S,5R)-4-(4-amino-2-oxo-2H-pyrimidin-1-yl)-3-oxa-bicyclo[3.1.0]hex-2-ylmethyl ester 
• 131267-40-8 1-O-Acetyl-5-O-benzoyl-2,3-dideoxy-2,3-methano-β-D-ribofuranose 
• 131267-39-5 (1R,4S,5S)-4-Benzoyloxymethyl-3-oxabicyclo<3.1.0>hexan-2-one 
• 131267-38-4 (1R,4S,5S)-4-Benzoyloxymethyl-3-oxa-7,8-diazabicyclo<3.3.0>oct-7-en-2-one 

Relevant articles and documents

Stereoselective photochemical 1,3-dioxolane addition to 5-alkoxymethyl-2(5H)-furanone: Synthesis of bis-tetrahydrofuranyl ligand for HIV protease inhibitor UIC-94017 (TMC-114)

A convenient synthesis of (3R,3aS,6aR)-3-hydroxyhexahydrofuro[2,3-b]furan, a high-affinity non-peptidal ligand for HIV protease inhibitor UIC-94017, is described. This inhibitor is undergoing advanced clinical trials. The synthesis utilizes a novel stereoselective photochemical 1,3-dioxolane addition to 5(S)-benzyloxymethyl-2(5H)-furanone as the key step. The requisite furanone derivative was prepared in high enantiomeric excess by an immobilized lipase-catalyzed selective acylation of (±)-1-(benzyloxy)-3-buten-2-ol and a ring-closing olefin metathesis with Grubbs' catalyst. Optically active bis-THF was converted to protease inhibitor 2 (UIC-94017).

A PRACTICAL SYNTHESIS OF 2-DEOXY ALDONOLACTONES VIA A SmI2-MEDIATED α-DEOXYGENATION REACTION

A one-step deoxygenation of 2-hydroxylactones or their acetates is possible using samarium diiodide as an electron-transfer reagent in conjunction with a proton source.