153751-46-3Relevant academic research and scientific papers
Ring-opened 4-hydroxy-δ-valerolactone subunit as a key structural fragment of polyesters that degrade without acid formation
Nifant'ev, Ilya E.,Shlyakhtin, Andrey V.,Bagrov, Vladimir V.,Ezhov, Roman N.,Lozhkin, Boris A.,Churakov, Andrei V.,Ivchenko, Pavel V.
, p. 629 - 631 (2018/12/13)
Random copolymers of ?-caprolactone with O-benzyl-protected 4-hydroxy- or 2,4-dihydroxy-δ-valerolactone after hydrogenation form γ-hydroxy functionalized polyesters that degrade via the cyclization to γ-butyrolactone fragments without carboxylic acid formation.
Metal-free oxidative esterification of benzylated monosaccharides
Camara, Tchambaga,Bil, Abed,Chagnault, Vincent
, p. 45 - 49 (2018/04/20)
Methyl glyconates have been attracting considerable attention as intermediates for the preparation of aryl C-glycosides, polyphenolic products, aliphatic polyesters, SGLT2 inhibitors, antibiotics etc … In view of the interest in those compounds, we report herein our work on the synthesis of methyl glyconates using an oxidative esterification carried out by molecular iodine. This reaction is catalyzed by non-toxic K4Fe(CN)6 that releases a small amount of cyanide ion into the reaction mixture. Four benzylated carbohydrates which contain a hemiacetalic functional group have been tested successfully.
Metal-free oxidative lactonization of carbohydrates using molecular iodine
Fusaro, Maxime B.,Chagnault, Vincent,Josse, Solen,Postel, Denis
, p. 5880 - 5883 (2013/07/25)
We describe herein the oxidative lactonization of fully or partially protected carbohydrates using molecular iodine. Oxidation of aldose hemiacetals is generally carried out by classical procedures, which are rarely chemo or regioselective. We recently re
C-2 Epimerization of aldonolactones promoted by magnesium iodide: a new way towards non-enzymatic epimerization
Gratien, Julie,Heck, Marie-Pierre,Mioskowski, Charles
, p. 18 - 30 (2008/09/18)
The first example of a non-enzymatic C-2 epimerization of aldonolactones is reported. The reaction of 2,3,4,6-tetra-O-benzyl-d-gluconolactone or 2,3,4,6-tetra-O-benzyl-d-mannonolactone with MgI2 in EtOH afforded their respective C-2 epimer. Studies conducted in EtOD showing the incorporation of a deuterium atom only at the C-2 position of the epimerized product reveal an epimerization rather than a racemization reaction. A mechanism involving a chelation with a magnesium species is proposed to explain this C-2 inversion reaction.
Palladium-catalyzed oxidation of benzylated aldose hemiacetals to lactones
Bessmertnykh, Alla,Henin, Francoise,Muzart, Jacques
, p. 1377 - 1380 (2007/10/03)
Benzyl protected sugar hemiacetals are oxidized to the corresponding lactones in excellent yields using bromobenzene, K2CO3 and the Pd(OAc)2/PPh3 catalytic system.
Enzymatic β-galactosidation of modified monosaccharides: Study of the enzyme selectivity for the acceptor and its application to the synthesis of disaccharides
Lopez,Fernandez-Mayoralas
, p. 737 - 745 (2007/10/02)
The selectivity of the E. coli β-galactosidase-catalyzed glycosylation of monosaccharides differently substituted at the anomeric position has been studied. Substituents bearing a phenyl ring increase the enzyme-acceptor binding; however, partial enzyme inhibition occurs. The regioselectivity of the glycosylation was dependent on small variations in the monosaccharide acceptor, such as the atom linked to the anomeric carbon and the number of methylenes between this atom and aromatic ring. A schematic model is proposed that accounts for the results. The information from this study allows the direct synthesis of disaccharides, with high regioselectivity and yields ranging from 30 to 40%.
