An improved regioselective preparation of methyl 2,3-di-O-acetyl-α,β-d-xylofuranoside

Abstract

Methyl 2,3-di-O-acetyl-α,β-d-xylofuranoside was prepared as the sole regioisomer in 63–72% yield, according to the applied mass of substrate, through a Candida antarctica lipase B catalysed alcoholysis of methyl 2,3,5-tri-O-acetyl-α,β-d-xylofuranoside. The product is a potential synthetic precursor for 5-modified xylofuranosides and 5′-modified xylonucleosides.

Keywords::

• Candida
• antarctica
• lipase B
• regioselectivity
• methyl 2,3-di-O-acetyl-α,β-d-xylofuranoside

Acknowledgements

We thank UNQ and SECyT (PICTO 06-36472) for financial support. AMI and LEI are research members of CONICET. We are grateful to Novozymes (Brazil) for the generous gift of CAL-B.

Declaration of interest: The authors report no conflicts of interest. The authors alone are responsible for the content and writing of the paper.