133435-77-5

Upstream product

• 172324-67-3 3-benzyloxymethyl-cyclobutanone 
• 797049-99-1 (5S,1'R)-2,2-dimethyl-5-(1'-benzyloxymethylcarboxymethyl)-1,3-dioxolan-4-one 
• 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 
• 797050-32-9 (2S,3R)-3-benzyloxymethyl-2-benzyloxy-methoxy-1,4-butanediol 
• 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 
• 133435-76-4 4-(benzyloxymethyl)-2(5H)-furanone 

Downstream Products

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

Relevant academic research and scientific papers

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.

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.

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.

Stereoselective synthesis and structure of butalactin and lactone II isolated from Streptomyces species

The synthesis and stereostructure of butalactin and lactone II isolated from streptomyces species was analyzed. It was observed that butalactin exhibited moderate antibacterial activity against gram positive bacteria. It was also observed that stereoselectivity of the lactones was in the ratio 8:1. The results show that an interesting rearrangement is formed due to intramolecular double esterification of 3-oxymethyl anion.

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.

Oxidation of some prochiral 3-substituted cyclobutanones using monooxygenase enzymes: a single-step method for the synthesis of optically enriched 3-substituted γ-lactones

Oxidation of the prochiral cyclobutanones 1-5 using Acinetobacter calcoaceticus NCIMB 9871 and Pseudomonas putida NCIMB 10007 monooxygenases (MO1 and MO2) furnishes the corresponding lactones 6-10 in moderate to excellent yield and enantiomeric purity.The

Asymmetric Reduction of 3-Hydroxymethylbutenolide Derivatives by Bakers' Yeast: A New Approach to the Synthesis of Factor-I

Bakers' yeast reduction of 3-benzyloxymethylbutenolide gave (S)-3-benzyloxymethylbutanolide, and its transformation to Factor-I, the autoregulator of Streptomyces viridocchromogenes, was examined.