78508-96-0Relevant articles and documents
AN EFFICIENT SYNTHESIS OF (S)-5-HYDROXYMETHYL-2(5H)-FURANONE
Vekemans, Jozef A. J. M.,Franken, Gabriel A. M.,Chittenden, Gordon J. F.,Godefroi, Erik F.
, p. 2299 - 2300 (1987)
A three step synthesis of the title compound 1a from D-ribono-1,4-lactone in 48percent yield is described.The concept centers on a novel NaHSO3-induced trans-Br-OAc elimination of the readily prepared bromo-acetate mixture 3a,b to the corresponding butenolides 1e and 1f, the former of which, on hydrolysis and purification, yields pure 1a.
Metal-containing zeolites as efficient catalysts for the transformation of highly valuable chiral biomass-derived products
Paris, Cecilia,Moliner, Manuel,Corma, Avelino
, p. 2101 - 2109 (2013)
Metal-containing zeolites, especially Sn-Beta, perform as very efficient heterogeneous catalysts in the selective oxidation of levoglucosenone, which is considered as a platform chemical for the production of highly-valuable chemicals, towards the synthesis of the optically pure γ-lactone (S)-γ-hydroxymethyl-α,β-butenolide (HBO) using H 2O2 as an oxidizing agent. Using Sn-Beta as a catalyst, yields up to 75% of (S)-γ-hydroxymethyl-α,β-butenolide are achieved in a one-pot cascade reaction. When Sn-Beta is combined with an acid resin, such as Amberlyst-15, the two-step process allows yields up to 90%.
Stereoselective Construction of the Methylcyclopentane Core of Peditithins B-H with Five Continuous Stereocenters
Li, Qingjiang,Li, Wei,Ni, Fu-Qiang,Wu, Shu-Qi,Yin, Sheng
supporting information, p. 9360 - 9364 (2020/12/21)
A stereoselective construction of the methylcyclopentane core (3) of jatrophane diterpenoids peditithins B-H was achieved in 14 steps from commercially available d-(+)-ribono-1,4-lactone (9). The linear 5-ene-heptanal derived from 9 was cyclized to the five-membered ring by an intramolecular carbonyl ene reaction, and five continuous stereocenters on 3 were stereoselectively introduced via a successive substrate-controlled manner, involving diastereoselective 1,4-addition, MoOPH-induced hydroxylation, and stereospecific epoxidation.
High-Yielding Diastereoselective syn-Dihydroxylation of Protected HBO: An Access to D-(+)-Ribono-1,4-lactone and 5-O-Protected Analogues
Moreaux, Maxime,Bonneau, Guillaume,Peru, Aurélien,Brunissen, Fanny,Janvier, Marine,Haudrechy, Arnaud,Allais, Florent
supporting information, p. 1600 - 1604 (2019/01/14)
A diastereoselective chemoenzymatic synthetic pathway to D-(+)-ribono-1,4-lactone, a versatile chiral sugar derivative widely used for the synthesis of various natural products, has been designed from cellulose-based levoglucosenone (LGO). This route involves a sustainable Baeyer-Villiger oxidation of LGO to produce enantiopure (S)-γ-hydroxymethyl-α,β-butenolide (HBO) that is further functionalized with various protecting groups to provide 5-O-protected γ-hydroxymethyl-α,β-butenolides. The latter then undergo a diastereoselective and high-yielding syn-dihydroxylation of the α,β-unsaturated lactone moiety followed by a deprotection step to give D-(+)-ribono-1,4-lactone. Through this 4-step synthetic route from LGO, D-(+)-ribono-1,4-lactone is obtained with d.r. varying from 82:18 to 97:3 and in overall yields between 32 and 41 % depending on the protecting group used. Moreover, valuable synthetic intermediates 5-O-tert-butyldimethylsilyl-, 5-O-tert-butyldiphenylsilyl- as well as 5-O-benzyl-ribono-1,4-lactones are obtained in 3 steps from LGO in 58, 61 and 40 %, respectively.
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.