An efficient chemoenzymatic route to methyl 4-O-benzyl-2,3-anhydro-beta-D-lyxopyranoside from methyl beta-D-xylopyranoside.
Methyl 4-O-benzyl-2,3-anhydro-beta-D-lyxopyranoside, an intermediate for the preparation of methyl beta-D-xylopyranoside derivatives modified at C-2, was obtained in five steps in 58% yield. The synthetic sequence starts from methyl beta-D-xylopyranoside through two main steps involving regioselective enzymatic acetylation and deacetylation catalyzed by lipase PS.
Mastihubová
Mária
M
Institute of Chemistry, Slovak Academy of Sciences, Dúbravská cesta 9, SK-845 38, Bratislava, Slovakia.
Mastihuba
Vladimír
V
Biely
Peter
P
D002236:Carbohydrate Conformation; D008759:Methylglycosides / Q000737:chemistry*; D015394:Molecular Structure; D010429:Pentoses / Q000138:chemical synthesis* / Q000737:chemistry*
D008759:Methylglycosides; D010429:Pentoses; C489874:methyl 4-O-benzyl-2,3-anhydrolyxopyranoside; C050519:methyl xylopyranoside