175416-92-9

Upstream product

• 108-05-4 vinyl acetate 
• 137726-46-6 (1RS,2RS,4SR,5SR)-Bicyclo<3.1.0>hexane-2,4-diol 
• 137726-52-4 (1RS,2RS,4SR,5SR)-Bicyclo<3.1.0>hex-2,4-diyl diacetate 
• 108-24-7 acetic anhydride 
• 137726-49-9 (1R,2R,4S,5S)-2-(tert-Butyl-dimethyl-silanyloxy)-4-trimethylsilanyloxy-bicyclo[3.1.0]hexane 
• 186581-53-3 diazomethane 
• 60410-16-4 (1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate 

Relevant academic research and scientific papers

Chemoenzymatic synthesis of carbocyclic nucleoside analogues with bicyclo[3.1.0]hexyl residues

The carbocyclic nucleoside analogues 8 and ent-8 have been prepared based on the enantiomerically pure bicyclo[3.1.0]hexane monoacetates 5 and ent-5 which were obtained by a lipase-catalysed asymmetrization of the meso-bicyclo[3.1.0]hexane derivatives 4 and 6, respectively. By an enantiodivergent approach both nucleoside analogues 8 and ent-8 have been synthesized starting from the common enantiomer 5. Furthermore, the adenine derivative ent-8 has been obtained from the monoacetate ent-5.

Lipase-Catalyzed Transesterification of meso-Cyclopentane Diols

The lipase-catalyzed transesterification of the meso-cyclopentane diols 1a - 6a with vinyl acetate in tetrahydrofuran/triethylamine in the presence of lipases of different origin has been investigated.Depending on the structure of the substrate and the origin of the lipase chiral cyclopentane derivatives with high enantiomeric excess could be obtained in good to excellent chemical yields. Key words: Lipase-catalyzed transesterifications; meso-cyclopentane diols; enantioselective acetylation; enzymes in organic solvents