Ontology highlight
ABSTRACT:
SUBMITTER: Hernandez-Torres JM
PROVIDER: S-EPMC1851890 | biostudies-other | 2004 Oct
REPOSITORIES: biostudies-other
The Journal of organic chemistry 20041001 21
The regioselective ring opening of pyranosidic 4,6-p-methoxybenzylidene acetals with BH(3)/Bu(2)BOTf in THF can be tuned by adjusting the reaction temperature and reagent concentrations. Reductive cleavage at 0 degrees C resulted in the exclusive formation of 4-O-p-methoxybenzyl (PMB) ethers, whereas reaction at -78 degrees C produced 6-O-PMB ethers in high yields. The latter condition was observed to be compatible with a variety of acid-sensitive functional groups, including allyl and enol ethe ...[more]