19377-75-4Relevant academic research and scientific papers
Formation of five-membered carbocycles from D-glucose: A Concise Synthesis of 4-Hydroxy-2-(hydroxymethyl)cyclopentenone
Koseki, Yoshitaka,Watanabe, Toshihiro,Kamishima, Takaaki,Kwon, Eunsang,Kasai, Hitoshi
, p. 1324 - 1328 (2019/09/18)
A concise synthesis of 4-hydroxy-2-(hydroxymethyl)cyclo-pentenone (1) has been accomplished from D-glucose by a three-step sequence that features a catalyst-free hydrothermal reaction of D-glucal, which is readily obtained from D-glucose. Optimization of the reaction conditions for synthesizing 1 was performed by changing the temperature and reaction time. The treatment of D-glucal under the optimal conditions, i.e., at 120 °C for 24 h, provided 1 in the highest isolated yield of 61%. 1 would become a versatile intermediate for the synthesis of various fine chemicals having a cyclopentenone structure from cellulosic biomass.
Dehydrogenation of 5-hydroxymethylfurfural to diformylfuran in compressed carbon dioxide: An oxidant free approach
Chatterjee, Maya,Ishizaka, Takayuki,Chatterjee, Abhijit,Kawanami, Hajime
, p. 1315 - 1326 (2017/08/15)
The dehydrogenation of biomass-based 5-hydroxymethylfurfural (HMF) to 2,5-diformylfuran (DFF) was achieved utilizing an activated carbon supported rhodium (Rh/C) catalyst under mild reaction conditions. The developed method successfully afforded complete conversion and the highest selectivity of DFF (>99%) without any additive, conventional hydrogen acceptor and oxidant. The efficiency of the method is achieved by the addition of compressed carbon dioxide (scCO2) and the synergistic effect of scCO2 and Rh/C, where scCO2 plays a pivotal role in accelerating the reaction by removing hydrogen, and consequently shifting the equilibrium to the forward direction. Optimization of different reaction parameters ensures the achievement of high conversion and selectivity. Characterization of the catalyst using different spectroscopic techniques suggests an interaction between the substrate and the catalyst and provides an indication of the possible reaction pathway, thus a mechanism would be outlined. The rate determining step of the reaction was calculated through mechanistic investigations involving theoretical calculations together with experimental analysis. One of the most attractive features of the method developed in this study is the reverse reaction of DFF, which can be achieved in one-pot without the addition of any external hydrogen. This process has successful application to the dehydrogenation of a variety of alcohols with different substituents.
Multicomponent cascade transformation of d -glucal to furan-appended triazole glycoconjugates
Yousuf, Syed Khalid,Taneja, Subhash Chandra,Mukherjee, Debaraj
supporting information; experimental part, p. 3097 - 3100 (2010/07/17)
Novel one-pot three- and four-component transformations of d-glucal to furan-based hydroxy triazole glycoconjugates have been achieved by sequential addition of reagents in the presence of Cu(OTf)2-Cu powder as catalysts. In general the carbohy
Synthesis of chiral unsaturated aminolactones using Pd-catalyzed allylic amination
Kallinen, Annukka,Tois, Jan,Sjoeholm, Rainer,Franzen, Robert
experimental part, p. 2367 - 2371 (2010/12/25)
Stereoselective synthesis of (5R,6R)- and (5S,6S)-5-benzylamino-6-(tert- butyldimethylsilanyloxymethyl)-5,6-dihydropyran-2-ones starting from d-glucal and furanaldehyde, respectively, is described. The synthesis relies on a Sharpless asymmetric dihydroxylation, an Achmatowicz reaction, and a stereoselective Pd-catalyzed allylic amination as the key steps.
Synthesis of enantiopure chloroalcohols by enzymatic kinetic resolution
Haak, Robert M.,Tarabiono, Chiara,Janssen, Dick B.,Minnaard, Adriaan J.,De Vries, Johannes G.,Feringa, Ben L.
, p. 318 - 323 (2008/03/27)
3-Alkenyl and heteroaryl chloroalcohols have been obtained in excellent enantiomeric excess (>99%) by enzymatic kinetic resolution using the haloalcohol dehalogenase HheC. Yields were close to the theoretical maximum for all substrates employed. Furthermo
Lipase-mediated preparation of enantiopure isolevoglucosenone
Kadota,ElAzab,Taniguchi,Ogasawara
, p. 1372 - 1374 (2007/10/03)
A route to enantiopure isolevoglucosenone, a regioisomer of levoglucosenone and a potential chiral building block, has been developed by employing lipase-mediated kinetic resolution as the key step.
Homologation of furfural and derivatives to furylacetaldehydes
Brochet,Syssa,Mouloungui,Delmas,Gaset
, p. 1735 - 1741 (2007/10/02)
The homologation of furfural 1a and methyl 3-(5-formyl-2-furyl) propenoate 1b or ethyl 3-(5-formyl-2-furyl) propenoate 1c to the corresponding furylacetaldehydes was carried out in two stages: i) preparation of the furan epoxides from 1a, 1b, 1c. ii) cleavage and rearrangement of the epoxides on sepiolite. Sepiolite is a convenient catalyst for this last stage involving substrates as labile as the furan epoxides.
Metal-mediated decarbonylation and dehydration of ketose sugars
Andrews, Mark A.
, p. 2703 - 2708 (2008/10/08)
Ketose sugars can be decarbonylated and/or dehydrated by the action of certain metal complexes. Fructose reacts with 1 equiv of RhCl(PPh3)3 (1) in N-methyl-2-pyrrolidinone (NMP) at 130°C to give furfuryl alcohol, Rh(CO)Cl(PPh3)2 (2), and a small amount of 1-deoxyerythritol. 1,3-Dihydroxyacetone consumes 2 equiv of 1, giving methane and ca. 2 mol of 2. With manno-2-heptulose the primary product is 2,7-anhydromanno-2-heptulopyranose. The mechanisms of these unusual reactions have been studied by using 13C-labeling experiments and model reactions employing Pd(II) and HCl. Attempts to make the reactions catalytic using [Rh(Ph2PCH2CH2CH2PPh 2)2]+[BF4]- in place of 1 were not successful. The use of NMP as a solvent offers some advantages in the acid-catalyzed synthesis of certain carbohydrate dehydration products, as exemplified by the conversion of manno-2-heptulose to its 2,7-anhydride and of 2-deoxyglucose to 1-(2-furanyl)-1,2-ethanediol.
NOVEL RING TRANSFER REACTION OF FURANS VIA INTRAMOLECULAR DIELS-ALDER REACTION OF ALLENE INTERMEDIATE: A NEW DOUBLE ANNULATION REACTION
Hayakawa, Kenji,Yamaguchi, Yasuchika,Kanematsu, Ken
, p. 2689 - 2692 (2007/10/02)
A novel ring transfer reaction of furans to fused furans by tandem intramolecular Diels-Alder reaction and base-catalyzed ring-opening of the adducts has been developed.
