133435-77-5

Basic information

• Product Name: 2(3H)-Furanone, dihydro-4-[(phenylmethoxy)methyl]-, (4S)-
• CAS NO: 133435-77-5
• Molecular Formula: C12H14O3
• Molecular Weight: 206.241
• Mol File: 133435-77-5.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 2(3H)-Furanone, dihydro-4-[(phenylmethoxy)methyl]-, (4S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2(3H)-Furanone, dihydro-4-[(phenylmethoxy)methyl]-, (4S)-(133435-77-5)
• EPA Substance Registry System: 2(3H)-Furanone, dihydro-4-[(phenylmethoxy)methyl]-, (4S)-(133435-77-5)

Safety Data

• Hazardous Substances Data: 133435-77-5(Hazardous Substances Data)

Usage

General Description

2(3H)-Furanone, dihydro-4-[(phenylmethoxy)methyl]-, (4S)- is a chemical compound with a furanone ring structure and a phenylmethoxy methyl group. It is also known as (4S)-dihydro-4-[(phenylmethoxy)methyl]-2(3H)-furanone. 2(3H)-Furanone, dihydro-4-[(phenylmethoxy)methyl]-, (4S)- is a chiral molecule, meaning it has a specific three-dimensional arrangement of its atoms. It is used in the fragrance industry and has a sweet, caramel-like odor. Additionally, it is found naturally in some fruits and vegetables and is responsible for their sweet aroma. This chemical compound is also being studied for its potential medicinal properties and as a potential flavoring agent.

Upstream product

• 81189-55-1 acetic acid 5-oxo-2,5-dihydrofuran-3-ylmethyl ester 
• 80904-75-2 4-hydroxymethyl-5H-furan-2-one 
• 383368-52-3 diethyl (2S,3R)-3-benzoyloxymethyl-2-benzyloxymethoxysuccinate 
• 383368-54-5 (2S,3S)-3-benzyloxymethyl-2,4-(4-methoxybenzylidenedioxy)butane-1-ol 
• 797050-33-0 (2S,3S)-3-benzyloxymethyl-2,4-(4-methoxybenzylidenedioxy)butanal 
• 383368-53-4 (2S,3R)-3-benzyloxymethyl-1,2,4-butanetriol 
• 383368-55-6 (2S,3S)-3-benzyloxymethyl-2-hydroxy-4-butanolide 
• 797050-35-2 (2S,3S)-3-benzyloxymethyl-2-methanesulfonyloxy-4-butanolide 
• 61934-55-2 3-bromomethyl-2-butenolide 
• 797050-32-9 (2S,3R)-3-benzyloxymethyl-2-benzyloxy-methoxy-1,4-butanediol 
• 797049-99-1 (5S,1'R)-2,2-dimethyl-5-(1'-benzyloxymethylcarboxymethyl)-1,3-dioxolan-4-one 
• 133435-76-4 4-(benzyloxymethyl)-2(5H)-furanone 
• 172324-67-3 3-benzyloxymethyl-cyclobutanone 

Downstream Products

• 240122-44-5 5-[(2S,3S,4S,5R)-3,4-Bis-benzyloxymethyl-5-(3,4-dimethoxy-phenyl)-tetrahydro-furan-2-yl]-benzo[1,3]dioxole 
• 240122-42-3 4-benzo[1,3]dioxol-5-yl-2,3-bis-benzyloxymethyl-4-hydroxy-N,N-dimethyl-butyramide 
• 240122-43-4 (3S,4S,5S)-5-Benzo[1,3]dioxol-5-yl-3,4-bis-benzyloxymethyl-dihydro-furan-2-one 
• 240122-41-2 4-benzyloxy-2-benzyloxymethyl-3-hydroxymethyl-N,N-dimethyl-butyramide 
• 192864-00-9 (3S,4S)-3,4-Bis-benzyloxymethyl-dihydro-furan-2-one 

Relevant articles and documents

Self-assembled ion-pair organocatalysis - Asymmetric Baeyer-Villiger oxidation mediated by flavinium-cinchona alkaloid dimer

An ion-pair catalyst generated by assembly of a chiral flavinium and a cinchona alkaloid dimer for use in asymmetric Baeyer-Villiger oxidation is presented. Ion-pair formation is essential for enhancing the catalytic activity and stereoselectivity. The catalyst is applicable to structurally diverse 3-substituted cyclobutanones, providing good to excellent enantioselectivities (up to 98: 2 e.r.). This study provides the first example of self-assembly of a flavin derivative and a base to form a chiral reaction site that enables a highly stereoselective reaction to occur.

Comparing the stereoselective biooxidation of cyclobutanones by recombinant strains expressing bacterial baeyer - Villiger monooxygenases

Microbial Baeyer - Villiger oxidation of representative prochiral ketones with a cyclobutanone structural motif was investigated using a collection of eight monooxygenases of different bacterial origin. This platform of enzymes is able to perform stereoselective biotransformations on an array of structurally diverse substrates. With several ketone precursors, biooxidations yielded enantiocomplementary butyrolactones as key intermediates for the synthesis of natural products and bioactive compounds. The microbial Baeyer - Villiger oxidation allows a facile and rapid entry to several compound classes in a desymmetrization reaction upon de novo generation of chirality.

Synthesis and absolute configuration of lactone II isolated from Streptomyces sp. Go 40/10

All four possible stereoisomers of lactone II isolated from Streptomyces sp. Go 40/10, an autoregulator, have been efficiently synthesized in a stereoselective manner starting from (S)-malic acid and sorbic acid, and the absolute configuration was determined to be 2S, 3S, 9R, 10S.