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78508-96-0Relevant academic research and scientific papers
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.
1,3-Dipolar cycloaddition reaction of α,β-unsaturated esters and lactones with diazomethane
Baskaran,Vasu,Prasad, Ram,Kodukulla,Trivedi, Girish K.,Chandrasekhar
, p. 4515 - 4526 (1996)
1,3-Dipolar cycloaddition of diazomethane to the α,β-unsaturated esters and lactones such as 2-4, 6-8, 10 and 13 occurs in a stereoselective manner affording conjugated Δ2-pyrazolines. E and Z isomers of D-mannitol lead to identical product which was cyclised to investigate the absolute stereochemistry of the product. The regiospecificities of all the reactions are consistent with FMO coefficients obtained through AM1 calculations.
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%.
Stereoselectivity of N-benzyl-C-ethoxycarbonyl nitrone cycloaddition to (S)-5-hydroxymethyl-2(5H)-furanone and its derivatives
Ondrus, Vladimir,Orsag, Michal,Fisera, L'ubor,Pronayova, Nad'a
, p. 10425 - 10436 (1999)
Stereoselectivity of the reaction of N-benzyl-C-ethoxycarbonyl nitrone (3) with (S)-5-hydroxymethyl-2(5H)-furanone (2a) and its 5-alkoxy substituted derivatives 2b-f was investigated. The reaction proceeds in a highly face- selective manner, the products 4-6 resulting from approach anti to the hydroxymethyl or alkoxymethyl group of the dipolarophile. The exo- stereoselectivity increases as the size of protective group attached to lactone (2b-f) increases. Endo-exo diastereoselectivity is affected significantly by the solvent. Microwave irradiation strongly accelerates the reaction with little effect on the diastereoselectivity to give the syn adduct 8a in addition to anti cycloadducts 4a-6a.
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.
Synthesis and fungicidal activity of methylsulfanylmethyl ether derivatives of levoglucosenone
Sharipov, Bulat T.,Davidova, Anna N.,Ryabova, Alena S.,Galimzyanova, Nailya F.,Valeev, Farid A.
, p. 31 - 37 (2019/02/25)
[Figure not available: see fulltext.] A series of derivatives were synthesized on the basis of levoglucosenone that contained hydroxy groups at the С-4 atom or С-2 and С-4 atoms or a hydroxy and methyl group at the С-4 atom. In addition, 4-hydroxymethylbutanolides were synthesized. Derivatives containing hydroxy groups were obtained as methylsulfanylmethyl ethers. It was established that compounds containing a 6,8-dioxabicyclo[3.2.1]-octane ring exhibited fungicidal activity against Rhizoctonia solani. It was shown that the presence of a methylsulfanylmethyl moiety in the ring could increase the fungicidal activity of compounds.
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.
METHOD FOR CONVERTING LEVOGLUCOSENONE INTO 4-HYDROXYMETHYL BUTYROLACTONE AND 4-HYDROXYMETHYL BUTENOLIDE WITHOUT USING ANY ORGANIC SOLVENT AND CATALYST
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Paragraph 0052-0056; 0057-0058; 0081-0084; 0085-0086, (2019/07/23)
The invention relates to a method for converting levoglucosenone into 4-hydroxymethyl butyrolactone and 4-hydroxymethyl butenolide without using any solvent or catalyst, wherein the oxidation and hydrolysis of the levoglucosenone or hydrogenated levoglucosenone are carried out in a single step using an aqueous solution of H2O2.
Assignment of the relative and absolute stereochemistry of two novel epoxides using NMR and DFT-GIAO calculations
Moraes,Alvarenga,Demuner,Viana
, p. 109 - 115 (2018/05/03)
Considering the potential biological application of isobenzofuranones, especially as agrochemical defensives, two novel epoxides, (1aR,2R,2aR,5S,5aS,6S,6aS)-5-(hydroxymethyl)hexahydro-2,6-methanooxireno[2,3-f]isobenzofuran-3(1aH)-one (9), and (1aS,2S,2aR,5S,5aS,6R,6aR)-5-(hydroxymethyl)hexahydro-2,6-methanooxireno[2,3-f]isobenzofuran-3(1aH)-one (10), were synthesized from the readily available D-mannitol in six steps. The multiplicities of the hydrogens located at the bridge of the bicycle are distinct for epoxides 9 and 10 due to W coupling, and this feature was employed to confirm the assignment of these nuclei. Besides analyses of the 2D NMR spectra, the assignments of the nuclei at the epoxide ring were also inferred from information obtained by theoretical calculations. The calculated 1H and 13C NMR chemical shifts for eight candidate structures were compared with the experimental chemical shifts of 9 and 10 by measuring the mean absolute errors (MAE) and by the DP4 statistical analysis. The structures and relative configurations of 9, and 10 were determined via NMR spectroscopy assisted with theoretical calculations. As consequence of the enantioselective syntheses starting from a natural polyol, the absolute configurations of the epoxides 9 and 10 were also defined.
Guiding a divergent reaction by photochemical control: Bichromatic selective access to levulinates and butenolides
Sutar, Revannath L.,Sen, Saumik,Eivgi, Or,Segalovich, Gal,Schapiro, Igor,Reany, Ofer,Lemcoff, N. Gabriel
, p. 1368 - 1374 (2018/02/09)
Allylic and acrylic substrates may be efficiently transformed by a sequential bichromatic photochemical process into derivatives of levulinates or butenolides with high selectivity when phenanthrene is used as a regulator. Thus, UV-A photoinduced cross-metathesis (CM) couples the acrylic and allylic counterparts and subsequent UV-C irradiation initiates E-Z isomerization of the carbon-carbon double bond, followed by one of two competing processes; namely, cyclization by transesterification or a 1,5-H shift and tautomerization. Quantum chemical calculations demonstrate that intermediates are strongly blue-shifted for the cyclization while red-shifted for the 1,5-H shift reaction. Hence, delaying the double bond migration by employing UV-C absorbing phenanthrene, results in a selective novel divergent all-photochemical pathway for the synthesis of fundamental structural motifs of ubiquitous natural products.
