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

Acid hydrolysis of 3,5-di- O-benzyl-1,2- O-cyclohexylidene-α- 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 t...

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Bibliographic Details
Published in:Carbohydrate research 1999-09, Vol.321 (1), p.110-115
Main Authors: Popsavin, Velimir, Grabež, Sanja, Stojanović, Biljana, Popsavin, Mirjana, Pejanović, Vjera, Miljković, Dušan
Format: Article
Language:English
Subjects:
1,2-Anhydro sugar
d-Lyxose
d-Lyxosides, protected
d-Xylofuranose, protected
Mutarotation
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Summary:Acid hydrolysis of 3,5-di- O-benzyl-1,2- O-cyclohexylidene-α- 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 α- d-lyxopyranoside or to d-lyxose.
ISSN:0008-6215
1873-426X
DOI:10.1016/S0008-6215(99)00164-0