85846-84-0Relevant articles and documents
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.
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.
