Deprotection of di-O-isopropylidene isocarbonucleosides.

MARTINEZ ESPERÓN, MARÍA F.; ERREA, MARÍA I.; MARTINS ALHO MIRIAM A.; D'ACCORSO NORMA B.

Arkivoc

ARKAT

Lugar: Suiza; Año: 2003 vol. X p. 491 - 499

1424-6376

Abstract Deprotection of 5-glycosyl heterocyclic derivatives of 1,2:3:4-di-O-isopropylidene-alfa-D-galacto- 1,6-hexadialdo-1,5-pyranose allowed isocarbonucleoside analogues to be obtained with enhaced solubility in the aqueous medium used for antiviral assays. Looking for a deprotection method of isopropylidene groups which would not affect the heterocycle, we performed and compared different deprotection techniques using microwave radiation or thermal heating and found that, in most cases, this goal could be achieved, in short times and good yields, when the reactions were microwave-assisted. O-isopropylidene-á-D-galacto- 1,6-hexadialdo-1,5-pyranose allowed isocarbonucleoside analogues to be obtained with enhaced solubility in the aqueous medium used for antiviral assays. Looking for a deprotection method of isopropylidene groups which would not affect the heterocycle, we performed and compared different deprotection techniques using microwave radiation or thermal heating and found that, in most cases, this goal could be achieved, in short times and good yields, when the reactions were microwave-assisted.