José M. Blanco

A useful synthesis of chiral sulfonyl cyanides: (1S,2S,5R)-2-isopropyl-5-methylcyclohexanesulfonyl cyanide

Abstract A convenient method for the preparation of chiral alkanesulfonyl cyanides, by oxidation of readily available alkyl thiocyanates with m -ClC 6 H 4 CO 3 H, has been developed.

The effect of the molecular weight of polyethylene glycol on the bioavailability of paracetamol-polyethylene glycol solid dispersions

A controlled study of the bioavailability of paracetamol in solid dispersion with PEG 6000, 10000 and 20000 has been made. The total amount of paracetamol excreted in urine increased with molecular weight of the PEG, but the rate of absorption of the drug was unaffected.

Divergent synthesis of two precursors of 3′-homo-2′-deoxy- and 2′-homo-3′-deoxy-carbocyclic nucleosides

Abstract Aminocyclopentanedimethanols 4 and 5 , which are of interest for the synthesis of higher homologues of 2′-deoxy- and 3′-deoxycarbonucleosides, respectively, were efficiently prepared by divergent routes starting from (±)-exo-bicyclo[2.2.1]hept-5-ene-2-carbaldehyde. In the key step, ammonolysis of the common intermediate (±)-(1β,3β,4α)-4-benzoyloxymethyl-1,3-cyclopentanedicarboxylic anhydride and subsequent esterification afford near-equimolar amounts of two easily separable isomeric carbamoyl esters.

A new, convenient synthesis of the chiral auxiliary (+)-8-phenylisomenthol

Abstract A new, straitghtforward and efficient method for preparing (+)-8-phenyl iso menthol 1 from its diastereomer (+)-8-phenyl isoneo menthol 2 is described. Conversion of 2 to (+)-8-phenyl-2-menthene 5 , followed by oxidation to the corresponding (+)- trans -epoxide 6 and reduction of 6 with LiBEt 3 H afforded 1 in 78% overall yield.

Synthesis of (±)-c-4-amino-r-1,t-2,c-3-cyclopentanetrimethanol and higher homologues of 8-azapurine arabino-carbocyclic nucleosides

Abstract (±)-c-4-Amino-r-1,t-2,c-3-cyclopentanetrimethanol ( 4 ) was synthesized from previously reported (±)-c-4,t-5-bis(benzoyloxymethyl)-r-1,c-3-cyclopentanedicarboxylic anhydride by methanolysis (which selectively esterified the less hindered carboxyl), oxidative degradation of the other to an amino group, and DIBAL-H reduction. Amino alcohol 4 was then converted into (±)-c-4-[(5-amino-6-chloropyrimidin-4-yl)amino]-r-1,t-2,c-3-cyclopentanetrimethanol, which was used for synthesis of 8-azapurine arabino-carbocyclic nucleoside analogues. Two N,N′-dicyclopentanylurea derivatives obtained as side products of the synthesis of 4 are also described.

Mass spectrometric investigation of 9,10-anthracenedione derivatives

The mass spectrometric behavior of some 9,10-anthracenedione derivatives is reported and discussed with the aid of metastable ion studies. In particular, mass spectrometry has allowed an easy distinction between the isomers bearing the sulfonamide group in different positions on the anthracenedione molecule.