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-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.
N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, Leninsky prosp., 47, 119991 Moscow, Russian Federation.
Nikita M
NM
Podvalnyy
Sergey L
SL
Sedinkin
Polina I
PI
Abronina
Alexander I
AI
Zinin
Ksenia G
KG
Fedina
Vladimir I
VI
Torgov
Leonid O
LO
Kononov
D001089:Arabinose / Q000031:analogs & derivatives* / Q000737:chemistry; D001565:Benzoates / Q000737:chemistry*; D002240:Carbohydrate Sequence; D008969:Molecular Sequence Data; D013865:Thioglycosides / Q000737:chemistry*
D001565:Benzoates; D013865:Thioglycosides; C431714:arabinofuranose; D001089:Arabinose