72605-53-9

Basic information

• Product Name: γ-benzyloxymethyl-α,β-butenolide
• Synonyms: γ-benzyloxymethyl-α,β-butenolide
• CAS NO: 72605-53-9
• Molecular Weight: 204.225
• Mol File: 72605-53-9.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: γ-benzyloxymethyl-α,β-butenolide(CAS DataBase Reference)
• NIST Chemistry Reference: γ-benzyloxymethyl-α,β-butenolide(72605-53-9)
• EPA Substance Registry System: γ-benzyloxymethyl-α,β-butenolide(72605-53-9)

Safety Data

• Hazardous Substances Data: 72605-53-9(Hazardous Substances Data)

Upstream product

• 78508-96-0 (5S)-5-(hydroxymethyl)-5H-furan-2-one 
• 100-39-0 benzyl bromide 
• 30725-00-9 2,3-O-isopropylidene-D-ribonic-γ-lactone 
• 5336-08-3 D-Ribono-1,4-lactone 
• 81927-55-1 O-benzyl 2,2,2-trichloroacetimidate 
• 37112-31-5 levoglucosenone 
• 78508-93-7 2,3-O-(ethoxymethylene)-D-ribonic acid γ-lactone 
• 103927-51-1 D-O-Benzyl-2-deoxyxylic acid 
• 99666-07-6 (3R,4R)-5-Benzyloxy-3,4-dihydroxy-pentanenitrile 
• 78513-07-2 (-)-(2S,3R)-2,3-epoxy-4-(benzyloxy)-1-butanol 
• 32780-08-8 (5S)-5-[(benzyloxy)methyl]dihydrofuran-2(3H)-one 
• 78508-91-5 5-benzyloxy-2-hydroxy-3-hydroxy-D-ribonolactone 
• 154230-51-0 (+/-)-3-acetoxy-4-benzyloxy-1-trimethylsilyl-1-butyne 
• 119046-45-6 (+/-)-4-benzyloxy-3-hydroxy-1-trimethylsilyl-1-butyne 

Downstream Products

• 72605-54-0 (+)-(2S,3S,4S)-2-piperonyl-3-(2-(3,4,5-trimethoxyphenyl)-1,3-dithiane-2-yl)-4-benzyloxymethyl-butan-4-olide 
• 114495-04-4 (3R,4S,2'S,3'R)-5,2'-Bis-benzyloxymethyl-4-methyl-tetrahydro-[3,3']bifuranyl-2,5'-dione 
• 94198-72-8 (4S,5S)-5-benzyloxymethyl-4-methyl-2(5H)-furanone 
• 111613-20-8 (2R,5S,6S)-5-benzyloxymethyl-4-oxa-exo-tricyclo<5.2.1.0^2.6>dec-8-en-3-one 
• 111533-92-7 (2R,5S,6S)-5-benzyloxymethyl-4-oxa-endo-tricyclo<5.2.1.0^2.6>dec-8-en-3-one 
• 32780-06-6 (5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran 
• 106795-91-9 (1R,6S,7S)-7-benzyloxymethyl-8-oxabicyclo<4.3.0>non-3-en-9-one 
• 111533-96-1 (1R,6S,7S)-4-methyl-7-benzyloxymethyl-8-oxabicyclo<4.3.0>non-3-en-9-one 
• 111533-97-2 (1R,6S,7S)-3-methyl-7-benzyloxymethyl-8-oxabicyclo<4.3.0>non-3-en-9-one 
• 681463-03-6 (4S,5S)-5-(benzyloxymethyl)-4-(1,3-dioxolan-2-yl)dihydrofuran-2-one 
• 156928-09-5 (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol 
• 253265-97-3 1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione 
• 206361-99-1 darunavir 
• 186488-54-0 (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl 4-nitrophenyl carbonate 

Relevant articles and documents

Intramolecular Photoreactions of (5S)-5-Oxymethyl-2(5H)-furanones as a Tool for the Stereoselective Generation of Diverse Polycyclic Scaffolds

The photoactivated evolution of a series of enantiomerically pure 5-oxymethyl-2(5H)-furanones has been investigated. The observed intramolecular photoreactions have proven to be a straightforward entry to diverse and stereochemically rich fragment-molecul

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).

Synthesis of optically active 4-benzyloxymethyl- and 4-(4-methoxyphenoxy)methylbuten-2-olides via lipase-mediated resolution

A new preparation of optically active 4-benzyloxymethyl- and 4-(4-methoxyphenoxy)methylbuten-2-olides has been developed by employing lipase-mediated resolution and palladium-mediated carbomethoxylation as key steps.