Abstract
The anomers methyl 2,3,5-tri- O-acetyl-α- d-ribofuranoside and methyl 2,3,5-tri- O-acetyl-β- d-ribofuranoside showed a different behaviour in the Candida antarctica B lipase-catalysed alcoholysis. While the enzymatic deprotection of the former proceeded regioselectively affording methyl 2,3-di- O-acetyl-α- d-ribofuranoside in 81% yield in 3 h at 45 °C showing no further transformation, the alcoholysis of the β-diasteromer was less selective. For this anomer, mixtures of partially acetylated products were formed, but contrasting to the α epimer, full deacetylated methyl β- d-ribofuranoside was quantitatively formed at long reaction times (5 days).
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