2744-05-0

Upstream product

• 935-79-5 cis-1,2,3,6-tetrahydrophthalic anhydride 
• 33240-34-5 cyclopentylmagnesium bromide 

Downstream Products

• 88586-06-5 (3aS,7aR)-3a,4,7,7a-tetrahydroisobenzofuran-1(3H)-one 
• 788121-64-2 (1S,6R)-6-Hydroxymethyl-cyclohex-3-enecarboxylic acid 
• 134785-23-2 (+/-)-cis-1-carbomethoxy-2-bromomethyl-4-cyclohexene 
• 88511-04-0 cis-(+/-)-α,α-Dimethyl-4-cyclohexen-1,2-dimethanol 
• 56799-24-7 (4R*,5R*)-4-hydroxymethyl-5-vinylcyclohexene 
• 88511-04-0 (1S-cis)-α,α-Dimethyl-4-cyclohexen-1,2-dimethanol 
• 130082-93-8 Methyl cis-6-<(phenylseleno)methyl>-1-(2-propenyl)-3-cyclohexenecarboxylate 
• 124804-06-4 2-Phenyl-1,3-dioxolo<4,5-f>perhydroisobenzofuran-5-on 
• 124804-10-0 (3aRS,4aSR,7aRS,8aSR)-4a-Methyl-2-phenyl-1,3-dioxolo<4.5-f>perhydro-isobenzofuran-5-on 
• 124804-11-1 4a-Trideuteromethyl-2-phenyl-1,3-dioxolo<4,5-f>perhydroisobenzofuran-5-on 

Relevant academic research and scientific papers

Simple Preparation of Rhodococcus erythropolis DSM 44534 as Biocatalyst to Oxidize Diols into the Optically Active Lactones

In the current study, we present a green toolbox to produce ecological compounds like lactone moiety. Rhodococcus erythropolis DSM 44534 cells have been used to oxidize both decane-1,4-diol (2a) and decane-1,5-diol (3a) into the corresponding γ- (2b) and δ-decalactones (3b) with yield of 80% and enantiomeric excess (ee)?=?75% and ee?=?90%, respectively. Among oxidation of meso diols, (?)-(1S,5R)-cis-3-oxabicyclo[4.3.0]non-7-en-2-one (5a) with 56% yield and ee?=?76% as well as (?)-(2R,3S)-cis-endo-3-oxabicyclo[2.2.1]dec-7-en-2-one (6a) with 100% yield and ee?=?90% were formed. It is worth mentioning that R. erythropolis DSM 44534 grew in a mineral medium containing ethanol as the sole source of energy and carbon Chirality 28:623–627, 2016.

Microbial alcohol dehydrogenase screening for enantiopure lactone synthesis: Down-stream process from microtiter plate to bench bioreactor

One-pot conversion with whole cells of bacteria was performed for biooxidation of meso monocyclic (3a-b) and bicyclic diols (3c-e) into corresponding chiral lactones of bicyclo[4.3.0]nonane structure (2a-b) as well as exo- and endo-bridged lactones with the structure of [2.2.1] (3c-d) and [2.2.2] (3e). Micrococcus sp. DSM 30771 was selected as biocatalyst with significant alcohol dehydrogenase activity. Among tested strains, microbial oxidation of meso diols 3a-e catalyzed by Micrococcus sp. afforded enantiomerically pure ((+)-(2S,3R)-2c (ee = 99%), (+)-(2S,3R)-2e (ee = 99%)) or enriched ((+)-(1S,5R)-2a (ee = 90%), (-)-(1S,5R)-2b (ee = 86%), (+)-(2S,3R)-2d (ee = 80%)) lactone moieties. Comparative study with respect to microbial cultivation as well as biooxidation was undertaken to verify agreement of secondary metabolite biosynthesis in different scales: from MTP (4 mL), across shake flask (100 mL) till bioreactor (4 L). The results from biotransformations showed quite similar dependence in oxidation of all substrates 3a-e in MTP and flasks as well, thereby confirmed the validity and reasonable approach of using MTP for preliminary studies.

REDUCTION DES ANHYDRIDES BICYCLIQUES CONDENSES PAR LE BROMURE DE CYCLOPENTYLMAGNESIUM

Greatly different product distributions were observed in the reactions of cyclopentyl- and isopropylmagnesium bromides with cyclohexane-, cyclohex-4-ene- and cyclobutane-1,2 dicarboxylic anhydrides.Cyclopentylmagnesium bromide yielded reduction products with high stereoselectivity whereas the isopropylmagnesium bromide provided the corresponding trans diastereomeric ketoacids via an addition enolization process.

Syntheses stereoselectives des γ-lactones bicycliques condensees

A highly stereoselective synthesis of trans/trans and cis/trans bicyclic γ-lactones is described using bicyclic dicarboxylic anhydrides.