Conversion of D-xylose to protected D-lyxose derivatives and to D-lyxose, via the corresponding 1,2-anhydride

Popsavin, V.; Grabez, S.; Stojanovic, B.; Popsavin, M.; Pejanovic, V.; Miljkovic, D.

Carbohydrate Research 321(1/2): 110-115


ISSN/ISBN: 0008-6215
DOI: 10.1016/s0008-6215(99)00164-0
Accession: 003393878

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Acid hydrolysis of 3,5-di-O-benzyl-1,2-O-cyclohexylidene- alpha -D-xylofuranose gave the corresponding lactol, which was subsequently converted to the 3,5-di-O-benzyl-2-O-mesyl-D-xylofuranose. This compound readily reacted with sodium methoxide, sodium benzylate or sodium hydroxide (presumably via the corresponding 1,2-anhydride) to give the protected D-lyxofuranosides. These compounds were finally converted to methyl alpha -D-lyxopyranoside or to D-lyxose.