Abstract
A new chemo-enzymatic route to tetra-O-acetyl-l-ribofuranose from d-lyxose is described. Lipase-catalyzed regioselective transesterification of acetate proceeded on C-4 of the d-lyxopyranoside. Subsequently, stereochemistry of liberated secondary alcohol was inverted by way of oxidation and reduction by IBX and NaBH(OAc)3 to give l-ribopyranoside. After deprotection, the furanose-pyranose isomeric mixture was converged to the target molecule, taking advantage of lipase-catalyzed preferential acetylation of primary alcohol on C-5.
Original language | English |
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Pages (from-to) | 197-200 |
Number of pages | 4 |
Journal | Journal of Molecular Catalysis B: Enzymatic |
Volume | 59 |
Issue number | 1-3 |
DOIs | |
Publication status | Published - 2009 Jul 1 |
Keywords
- Lipase
- Regioselective reaction
- Stereochemical inversion
- d-Lyxose
- l-Nucleoside
- l-Ribose
ASJC Scopus subject areas
- Catalysis
- Bioengineering
- Biochemistry
- Process Chemistry and Technology