172796-28-0

Basic information

• Product Name: 2(3H)-Furanone, dihydro-4-[(phenylmethoxy)methyl]-, (4R)-
• CAS NO: 172796-28-0
• Molecular Formula: C12H14O3
• Molecular Weight: 206.241
• Mol File: 172796-28-0.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 2(3H)-Furanone, dihydro-4-[(phenylmethoxy)methyl]-, (4R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2(3H)-Furanone, dihydro-4-[(phenylmethoxy)methyl]-, (4R)-(172796-28-0)
• EPA Substance Registry System: 2(3H)-Furanone, dihydro-4-[(phenylmethoxy)methyl]-, (4R)-(172796-28-0)

Safety Data

• Hazardous Substances Data: 172796-28-0(Hazardous Substances Data)

Upstream product

• 81189-55-1 acetic acid 5-oxo-2,5-dihydrofuran-3-ylmethyl ester 
• 80904-75-2 4-hydroxymethyl-5H-furan-2-one 
• 61934-55-2 3-bromomethyl-2-butenolide 
• 172324-67-3 3-benzyloxymethyl-cyclobutanone 
• 133435-76-4 4-(benzyloxymethyl)-2(5H)-furanone 

Downstream Products

• 192213-99-3 (S)-1-Benzyl-3-benzyloxymethyl-pyrrolidine 
• 192214-04-3 (R)-1-Benzyl-3-benzyloxymethyl-pyrrolidine 
• 192214-05-4 benzyl (R)-3-(hydroxymethyl)pyrrolidine-1-carboxylate 
• 192213-98-2 Methanesulfonic acid (R)-2-benzyloxymethyl-4-methanesulfonyloxy-butyl ester 
• 192214-03-2 (R)-1-Benzyl-4-benzyloxymethyl-pyrrolidin-2-one 
• 192214-01-0 Toluene-4-sulfonic acid (S)-5-oxo-tetrahydro-furan-3-ylmethyl ester 
• 5082-74-6 (R)-(+)-3-(hydroxymethyl)pyrrolidine 
• 124391-76-0 -(+)-methanol 
• 192214-00-9 (S)-1-((benzyloxy)carbonyl)pyrrolidine-3-carboxylic acid 
• 192214-06-5 (R)-1-((benzyloxy)-carbonyl)pyrrolidine-3-carboxylic acid 
• 78914-69-9 (S)-(-)-N-benzylpyrrolidine-2-methanol hydrochloride 
• 72580-53-1 (S)-(+)-3-pyrrolidinecarboxylic acid 
• 110013-19-9 (S)-(-)-3-(hydroxymethyl)pyrrolidine 
• 337968-47-5 (3R,4R,5S)-5-Benzo[1,3]dioxol-5-yl-3-[benzo[1,3]dioxol-5-yl-(tert-butyl-dimethyl-silanyloxy)-methyl]-4-benzyloxymethyl-tetrahydro-furan-2-ol 

Relevant articles and documents

Preparation of chiral 4-benzyloxymethyldihydrofuran-2-one using lipase-catalyzed kinetic resolution: Synthesis of (-)-virginiae butanolide C (VB C)

Lipase-catalyzed kinetic resolution of the N,N-dialkyl-3-benzyloxymethyl-4-hydroxybutanamide 10a,b afforded the acetate 11a,b with (R) configuration, whereas the N-monoalkyl-3-benzyloxymethyl-4-hydroxybutanamide 10c-e gave the acetate 11c-e with (S) configuration. The butanamide 10 smoothly cyclized to give chiral 4-benzyloxymethyldihydrofuran-2-one 9 without racemization, which was effectively transformed into highly stereocontrolled virginiae butanolide C (VB C).

Baeyer–Villiger monooxygenase-catalyzed desymmetrizations of cyclobutanones. Application to the synthesis of valuable spirolactones

A series of γ-butyrolactone derivatives, including some spiranic ones, was obtained through desymmetrization of the corresponding prochiral 3-substituted cyclobutanones via Baeyer–Villiger monooxygenase (BVMO)-catalyzed oxidation. After reaction optimization using several commercial enzymes, both antipodes of various lactones were synthesized in most cases with >90% conversion and >80% enantiomeric excess under mild reaction conditions. In some cases alcohol formation was also observed (up to 40% conversion) as an undesired side reaction due to the presence of alcohol dehydrogenases in these preparations. Selected transformations were achieved on a 100 mg scale showing the possibilities of these oxidative biocatalysts as a new source of highly interesting compounds.

Enantiodivergent chemoenzymatic synthesis of (R)- and (S)-β-proline in high optical purity

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