681463-02-5

Basic information

• Product Name: 2-Propenoic acid, (1S)-1-[(phenylmethoxy)methyl]-2-propenyl ester
• CAS NO: 681463-02-5
• Molecular Formula: C14H16O3
• Molecular Weight: 232.279
• Mol File: 681463-02-5.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 2-Propenoic acid, (1S)-1-[(phenylmethoxy)methyl]-2-propenyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Propenoic acid, (1S)-1-[(phenylmethoxy)methyl]-2-propenyl ester(681463-02-5)
• EPA Substance Registry System: 2-Propenoic acid, (1S)-1-[(phenylmethoxy)methyl]-2-propenyl ester(681463-02-5)

Safety Data

• Hazardous Substances Data: 681463-02-5(Hazardous Substances Data)

Usage

Formation

Ester formed from the condensation of 2-propenoic acid and (1S)-1-[(phenylmethoxy)methyl]-2-propenyl alcohol

Common uses

Production of polymers, coatings, adhesives, industrial products, synthesis of pharmaceutical intermediates

Physical properties

Colorless to pale yellow liquid, characteristic odor

Toxicity

Considered to have low toxicity

Potential applications

Flavoring agent in food products

Upstream product

• 233670-05-8 (R)-1-(benzyloxy)but-3-en-2-yl acetate 
• 93553-66-3 1-(benzyloxy)but-3-en-2-ol 
• 60656-87-3 benzyloxyacetoaldehyde 
• 109613-59-4 (S)-1-(benzyloxy)but-3-en-2-ol 
• 814-68-6 acryloyl chloride 

Downstream Products

• 681463-03-6 (4S,5S)-5-(benzyloxymethyl)-4-(1,3-dioxolan-2-yl)dihydrofuran-2-one 
• 186488-54-0 (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl 4-nitrophenyl carbonate 
• 206361-99-1 darunavir 
• 253265-97-3 1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione 
• 156928-09-5 (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol 
• 72605-53-9 γ-benzyloxymethyl-α,β-butenolide 

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).