1353637-78-1

Basic information

• Product Name: (4S,5R)-4-dimethyl(phenyl)silyl-5-ethyl-4,5-dihydrofuran-2(3H)-one
• Synonyms: (4S,5R)-4-dimethyl(phenyl)silyl-5-ethyl-4,5-dihydrofuran-2(3H)-one
• CAS NO: 1353637-78-1
• Molecular Weight: 248.397
• Mol File: 1353637-78-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (4S,5R)-4-dimethyl(phenyl)silyl-5-ethyl-4,5-dihydrofuran-2(3H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: (4S,5R)-4-dimethyl(phenyl)silyl-5-ethyl-4,5-dihydrofuran-2(3H)-one(1353637-78-1)
• EPA Substance Registry System: (4S,5R)-4-dimethyl(phenyl)silyl-5-ethyl-4,5-dihydrofuran-2(3H)-one(1353637-78-1)

Safety Data

• Hazardous Substances Data: 1353637-78-1(Hazardous Substances Data)

Upstream product

• 2407-43-4 5-ethyl-5H-furan-2-one 
• 185990-03-8 dimethylphenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane 
• 130247-53-9 ethyl 2-ethoxycarbonyl-3-dimethyl(phenyl)silyl-2-propenoate 

Relevant articles and documents

Stereoselective Synthesis of Polysubstituted Tetrahydropyranones via Acid-Promoted Cyclization of β-Silyl-γ-ethylidene-γ-butyrolactones with Aldehydes and Ketones

β-Silyl-γ-ethylidene-γ-butyrolactone upon one-pot treatment with aldehydes and ketones in the presence of Lewis acids underwent a tandem Hosomi-Sakurai/Prins cyclization to give polysubstituted tetrahydropyranones stereoselectively. Various aldehydes and ketones can be used in this reaction to produce the corresponding tetrahydropyranones. The optical purity of the starting γ-butyrolactone was substantially retained in the resulting tetrahydropyranones.

Organo-catalyzed enantioselective synthesis of some β-silyl γ-alkyl γ-butyrolactones as intermediates for natural products

The enantioselective synthesis of some β-silyl γ-alkyl γ-butyrolactones has been achieved by an organo-catalyzed Michael addition of enolizable aldehydes onto a silylmethylene malonate followed by a silicon-facilitated Bayer-Villiger oxidation of the β-silyl aldehyde adducts as the key step. γ-Alkyl γ-butenolides were obtained from the β-silyl γ-alkyl γ-butyrolactones by Fleming-Tamao oxidation of the silyl group to a hydroxy group and subsequent elimination. These butenolides are the advanced intermediates of some natural products such as (+)-γ-caprolactone, (+)-methylenolactocine, and (-)-quercus lactone.