Barlow, Thomas published the artcileAralkylation of Guanosine with p-Substituted Styrene Oxides, Formula: C8H9BrO2, the main research area is aralkylation guanosine styrene oxide.
To probe mechanisms of nucleoside aralkylation, product distributions and product stereochemistries were determined in reactions of optically active p-methyl- and p-bromo-styrene oxide with guanosine. The proportion of 7-, N2- and O6-substituted guanosine products was 0.32:0.62:0.06 in neutral, aqueous reactions of the (R) p-methylstyrene oxide and 0.85:0.09:0.04 in reactions with the (R) p-bromostyrene oxide. The exocyclic positions opened The epoxide at the α-carbon. Epoxide ring-opening by the nitrogen at the 7-position showed little preference for the α- or β-carbons in reactions with p-methylstyrene oxide. However, the p-bromostyrene oxide favored reaction at the β-carbon almost 4-fold over reaction at the α-carbon. Almost total inversion of stereochem. was found to occur in reactions at the 7-position. In contrast, the ratio of inversion to retention of configuration in N- and O-substituted products was 2:1 and 1:1 for reactions with the p-methylstyrene oxide and 6:1 and 3:1 for reactions with p-bromostyrene oxide, resp. These experiments suggest that an SN2 mechanism is in effect with reactions at the 7-position, whereas substrates of an increasingly ionic nature are involved in reactions at the N2- and O6- positions, resp.
Chemical Research in Toxicology published new progress about Aralkylation. 92093-23-7 belongs to class alcohols-buliding-blocks, name is 1-(4-Bromophenyl)ethane-1,2-diol, and the molecular formula is C8H9BrO2, Formula: C8H9BrO2.
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