78376-11-1

Basic information

• Product Name: (5RS)-5-[(RS/SR)-1-hydroxybenzyl]-4-methoxyfuran-2(5H)-one
• Synonyms: (5RS)-5-[(RS/SR)-1-hydroxybenzyl]-4-methoxyfuran-2(5H)-one
• CAS NO: 78376-11-1
• Molecular Weight: 220.225
• Mol File: 78376-11-1.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: (5RS)-5-[(RS/SR)-1-hydroxybenzyl]-4-methoxyfuran-2(5H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: (5RS)-5-[(RS/SR)-1-hydroxybenzyl]-4-methoxyfuran-2(5H)-one(78376-11-1)
• EPA Substance Registry System: (5RS)-5-[(RS/SR)-1-hydroxybenzyl]-4-methoxyfuran-2(5H)-one(78376-11-1)

Safety Data

• Hazardous Substances Data: 78376-11-1(Hazardous Substances Data)

Upstream product

• 69556-70-3 4-methoxy-5H-furan-2-one 
• 100-52-7 benzaldehyde 
• 3510-99-4 3-methoxy-but-2-enoic acid ethyl ester 
• 1116-51-4 ethyl χ-bromo-β-methoxycrotonate 
• 86268-15-7 methyl 5-lithiotetronate 
• 82204-15-7 4-methoxy-2-(trimethylsilyloxy)furan 

Downstream Products

• 72031-58-4 (Z)-4-methoxy-5-benzylidenefuran-2(5H)-one 
• 78819-23-5 5,6-Z-fadyenolide 
• 78819-24-6 5,5-E-fadyenolide 
• 100074-92-8 4-methoxy-3-phenyl-5-(phenylmethylene)furan-2(5H)-one 
• 1448595-40-1 (Z)-3-bromo-5-(bromo(phenyl)methylene)-4-methoxyfuran-2(5H)-one 
• 1448595-41-2 (E)-3-bromo-5-(bromo(phenyl)methylene)-4-methoxyfuran-2(5H)-one 
• 1448595-39-8 3,5-dibromo-5-(bromo(phenyl)methyl)-4-methoxyfuran-2(5H)-one 
• 1448595-30-9 (Z)-5-benzylidene-3-bromo-4-methoxyfuran-2(5H)-one 
• 82204-21-5 methyl 5-(1-methoxybenzyl)tetronate 

Relevant articles and documents

A Rapid Entry to Diverse γ-Ylidenetetronate Derivatives through Regioselective Bromination of Tetronic Acid Derived γ-Lactones and Metal-Catalyzed Postfunctionalization

The synthesis of a series of diverse methyl and benzyl γ-ylidenetetronate derivatives was accomplished through the condensation of methyl and benzyl tetronates with (hetero)aryl aldehydes in a new two- or three-step aldolisation/dehydration sequence. The bromination of methyl and benzyl γ-ylidenetetronates occurred under mild conditions to provide the corresponding C-3-brominated γ-unsaturated lactones. Di- and tribrominated γ-lactones were prepared under slightly different conditions. Some brominated materials were employed in representative Stille, Suzuki-Miyaura, and Sonogashira cross-coupling reactions to yield functionalized methyl and benzyl γ-ylidenetetronate derivatives. Compounds that resulted from the Sonogashira cross-coupling reactions were desilylated and converted into 1,2,3-triazole derivatives through a copper(I)-catalyzed 1,3-dipolar cycloaddition reaction with benzyl azide.

Highly regioselective 3-hydroxyalkylations of boron 4-methoxy-2-furanolates: A new entry to 5-unsubstituted and 5-monosubstituted 3-acyl-4-o-methyl tetronates

Boron 4-methoxy-2-furanolates generated in situ from 5-unsubstituted and 5-monosubstituted 4-O-methyl tetronates undergo highly regioselective 3-hydroxyalkylations with aldehydes to give 5-unsubstituted and 5-monosubstituted 3-acyl-4-O-methyl tetronates, respectively, in good overall yields after oxidation of the intermediate alcohols with 2-iodoxybenzoic acid.

Synthetic Routs to the Piperolides, Faydenolides, Epoxypiperolides, and Related Compounds

Syntheses of the piperolides, the faydenolides, epoxypiperolide, and related compounds are described. (+/-)-Narthogenin is also efficiently produced.