A wide range of aromatic ketones can be hydrogenated with high conversion and generally good to e... more A wide range of aromatic ketones can be hydrogenated with high conversion and generally good to excellent enantioselectivity in the presence of the title ligand.
Hyperbranched polymers represent an important part of the family of dendritic and multibranched p... more Hyperbranched polymers represent an important part of the family of dendritic and multibranched polymers, whose properties are indeed strongly detd. by the nature of their terminal groups. The incorporation of glycolipid moieties to these scaffolds creates a new family of glycolipid- based hyperbranched structures. Indeed, the intrinsic microheterogenicity of these hyperbranched dendritic polymers would potentially mimic microdomain formation in lipid membranes which is typically assocd. with important cellular events such as signaling, vesicle fusion, and pathogen invasion among others. In this context we have developed new methods of enantioselective synthesis of sphingosines and ceramides modified at the fatty acid chain with terminal N3 groups. Dendritic hyperbranched structures based on Boltorn H30 to which b- GalCer- N3 and other lipidic units were attached, were prepd. by using Cu(I) - catalyzed [3+2] alkyne- azide cycloaddn. The inhibition study of these multivalent systems ...
ABSTRACT ChemInform is a weekly Abstracting Service, delivering concise information at a glance t... more ABSTRACT ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
ABSTRACT We have reinvestigated the reaction of α-pyranosides-2-uloses 13, 14, 19 and 24 with DAS... more ABSTRACT We have reinvestigated the reaction of α-pyranosides-2-uloses 13, 14, 19 and 24 with DAST and shown that the 1,2-difluorinated compounds 17, 18 and 25 are produced by a ring-contraction reaction. The reaction of 18 with benzyl alcohol gives the tri-benzyl derivative 26 or compound 27, depending on the reaction conditions. Treating 17 with 2-naphthol produced the spiranic compounds 29–31. The reaction of 17 with bis(trimethylsilyl)uracil produced the mononucleoside 28, which preserves the fluorine atom in the more substituted carbon.
The synthesis of 2″-deoxy-2″-fluoro-adenophostin A framework starting from tri-O-acetylglucal and... more The synthesis of 2″-deoxy-2″-fluoro-adenophostin A framework starting from tri-O-acetylglucal and adenosine is described. The key steps are the formation of the 2-deoxy-2-fluoroglycosyl donor by electrophilic fluorination of tri-O-acetylglucal and the stereoselective glycosylation of a suitable adenosine derivative. The glycosylation reaction was optimized affording the desired 2″-deoxy-2″-fluoroglycoside with excellent α-stereoselectivity and in good yields, taking into account that glycosylations using nucleosides as glycosyl acceptors do not usually give excellent results. In that sense, an improvement of the glycosylation step with respect to that of the reported adenophostin synthesis, using adenosine derivatives as glycosyl donors, has been made.
D- and L-carbocyclic nucleosides were obtained by a new procedure involving an enantioselective r... more D- and L-carbocyclic nucleosides were obtained by a new procedure involving an enantioselective rhodium/duphos-catalyzed hydroacylation reaction as the key step. The 3-hydroxymethyl-cyclopentanol intermediate was obtained by stereoselective reduction of ketone and by dynamic kinetic resolution (DKR).
A wide range of aromatic ketones can be hydrogenated with high conversion and generally good to e... more A wide range of aromatic ketones can be hydrogenated with high conversion and generally good to excellent enantioselectivity in the presence of the title ligand.
Hyperbranched polymers represent an important part of the family of dendritic and multibranched p... more Hyperbranched polymers represent an important part of the family of dendritic and multibranched polymers, whose properties are indeed strongly detd. by the nature of their terminal groups. The incorporation of glycolipid moieties to these scaffolds creates a new family of glycolipid- based hyperbranched structures. Indeed, the intrinsic microheterogenicity of these hyperbranched dendritic polymers would potentially mimic microdomain formation in lipid membranes which is typically assocd. with important cellular events such as signaling, vesicle fusion, and pathogen invasion among others. In this context we have developed new methods of enantioselective synthesis of sphingosines and ceramides modified at the fatty acid chain with terminal N3 groups. Dendritic hyperbranched structures based on Boltorn H30 to which b- GalCer- N3 and other lipidic units were attached, were prepd. by using Cu(I) - catalyzed [3+2] alkyne- azide cycloaddn. The inhibition study of these multivalent systems ...
ABSTRACT ChemInform is a weekly Abstracting Service, delivering concise information at a glance t... more ABSTRACT ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
ABSTRACT We have reinvestigated the reaction of α-pyranosides-2-uloses 13, 14, 19 and 24 with DAS... more ABSTRACT We have reinvestigated the reaction of α-pyranosides-2-uloses 13, 14, 19 and 24 with DAST and shown that the 1,2-difluorinated compounds 17, 18 and 25 are produced by a ring-contraction reaction. The reaction of 18 with benzyl alcohol gives the tri-benzyl derivative 26 or compound 27, depending on the reaction conditions. Treating 17 with 2-naphthol produced the spiranic compounds 29–31. The reaction of 17 with bis(trimethylsilyl)uracil produced the mononucleoside 28, which preserves the fluorine atom in the more substituted carbon.
The synthesis of 2″-deoxy-2″-fluoro-adenophostin A framework starting from tri-O-acetylglucal and... more The synthesis of 2″-deoxy-2″-fluoro-adenophostin A framework starting from tri-O-acetylglucal and adenosine is described. The key steps are the formation of the 2-deoxy-2-fluoroglycosyl donor by electrophilic fluorination of tri-O-acetylglucal and the stereoselective glycosylation of a suitable adenosine derivative. The glycosylation reaction was optimized affording the desired 2″-deoxy-2″-fluoroglycoside with excellent α-stereoselectivity and in good yields, taking into account that glycosylations using nucleosides as glycosyl acceptors do not usually give excellent results. In that sense, an improvement of the glycosylation step with respect to that of the reported adenophostin synthesis, using adenosine derivatives as glycosyl donors, has been made.
D- and L-carbocyclic nucleosides were obtained by a new procedure involving an enantioselective r... more D- and L-carbocyclic nucleosides were obtained by a new procedure involving an enantioselective rhodium/duphos-catalyzed hydroacylation reaction as the key step. The 3-hydroxymethyl-cyclopentanol intermediate was obtained by stereoselective reduction of ketone and by dynamic kinetic resolution (DKR).
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Papers by M. Matheu