85846-84-0Relevant academic research and scientific papers
A METHOD FOR EASY PREPARATION OF OPTICALLY PURE (S)-5-HYDROXY-2-PENTEN-4-OLIDE AND (S)-5-HYDROXYPENTAN-4-OLIDE
Koseki, Koshi,Ebata, Takashi,Kawakami, Hiroshi,Matsushita, Hajime,Naoi, Yoshitake,Itoh, Kazuo
, p. 423 - 426 (1990)
A new method for preparation of (S)-5-hydroxy-2-penten-4-olide 1 and (S)-5-hydroxypentan-4-olide 8 starting from levoglucosenone 2 is described.
Organic solvent- and catalyst-free Baeyer-Villiger oxidation of levoglucosenone and dihydrolevoglucosenone (Cyrene): A sustainable route to (: S)-γ-hydroxymethyl-α,β-butenolide and (S)-γ-hydroxymethyl-γ-butyrolactone
Bonneau, Guillaume,Peru, Aurélien A. M.,Flourat, Amandine L.,Allais, Florent
supporting information, p. 2455 - 2458 (2018/06/11)
A straightforward and sustainable route to (S)-γ-hydroxymethyl-α,β-butenolide (HBO) and (S)-γ-hydroxymethyl-α,β-butyrolactone (2H-HBO), two valuable chemical platforms for the synthesis of fine chemicals such as drugs, pheromones, flavors and fragrances, has been optimized using renewable cellulose-based levoglucosenone (LGO) and Cyrene as starting materials and aqueous H2O2 as both a solvent and an oxidizing agent. Combined with short-path distillation, this procedure provides enantiopure HBO and 2H-HBO in yield as high as 72% at the kilo scale.
Chemo-enzymatic synthesis of key intermediates (S)-γ-hydroxymethyl-α,β-butenolide and (S)-γ-hydroxymethyl-γ-butyrolactone via lipase-mediated Baeyer-Villiger oxidation of levoglucosenone
Flourat,Peru,Teixeira,Brunissen,Allais
, p. 404 - 412 (2018/04/16)
Levoglucosenone (LGO), a valuable chiral platform chemical that can be efficiently produced from catalytic fast pyrolysis of cellulose, has been efficiently converted into optically pure (S)-γ-hydroxymethyl-α,β-butenolide (HBO) using a two-step sequence involving a lipase-mediated Baeyer-Villiger oxidation and an acid hydrolysis. In the same fashion, (S)-γ-hydroxymethyl-γ-butyrolactone (2H-HBO) was successfully obtained through a three-step sequence (Baeyer-Villiger, palladium-catalysed hydrogenation and acid hydrolysis). The use of solid buffers in the lipase-mediated Baeyer-Villiger oxidation has proved beneficial in two ways: not only the reaction time and the enzymatic load were both reduced four-fold (from 8 to 2 hours and 464 to 113 U mmol?1) to reach conversions ≥83%, but solid buffers also prevented lipase from denaturation, thus preserving its enzymatic activity and allowing its use for further oxidation cycles.
