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Ring opening of acylated β- d-arabinofuranose 1,2,5-orthobenzoates with nucleophiles allows access to novel selectively-protected arabinofuranose building blocks

β- d-Arabinofuranose 1,2,5-orthobenzoates with 3- O-acetyl, 3- O-benzoyl, and 3- O-chloroacetyl groups were prepared in an efficient manner starting from readily available crystalline methyl 2,3,5-tri- O-benzoyl-α- d-arabinofuranoside, and ring-opening reactions of these compounds with O- and S-nucl...

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Bibliographic Details
Published in:Carbohydrate research 2011-01, Vol.346 (1), p.7-15
Main Authors: Podvalnyy, Nikita M., Sedinkin, Sergey L., Abronina, Polina I., Zinin, Alexander I., Fedina, Ksenia G., Torgov, Vladimir I., Kononov, Leonid O.
Format: Article
Language:English
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Summary:β- d-Arabinofuranose 1,2,5-orthobenzoates with 3- O-acetyl, 3- O-benzoyl, and 3- O-chloroacetyl groups were prepared in an efficient manner starting from readily available crystalline methyl 2,3,5-tri- O-benzoyl-α- d-arabinofuranoside, and ring-opening reactions of these compounds with O- and S-nucleophiles were studied. Optimized conditions leading to the formation of the respective monosaccharide adducts (up to 96% isolated yields) and to α-(1→5)-linked disaccharide thioglycosides with 5′-OH unprotected (up to 30% isolated yields) were found. Basing on these results, a novel approach for effective differentiation of 3,5-diol system and 2-hydroxy group in arabinofuranose thioglycosides was proposed. The selectively protected derivatives prepared are valuable building blocks for the assembly of linear and branched oligoarabinofuranosides.
ISSN:0008-6215
1873-426X
DOI:10.1016/j.carres.2010.11.002