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  • Title: Regioselective and stereocontrolled syntheses of protected L-glycosides from L-arabinofuranosides.
    Author: Sivets GG.
    Journal: Carbohydr Res; 2020 Feb; 488():107901. PubMed ID: 31911361.
    Abstract:
    Synthesis of novel mono- and di-O-protected l-arabinofuranoside derivatives was described via regioselective base-catalyzed acylations of methyl α- and β-l-arabinofuranosides with acyl chlorides. A new method for selective 3(2)-O-acylation of 5-O-silyl (trityl) l-arabinofuranosides was investigated based upon generation of organoboron compounds using l-Selectride and subsequent reaction of salt carbohydrate species with pivaloyl or 4-chlorobenzoyl chloride as the electrophile. Syntheses of methyl 2,3-anhydro-l-furanosides were accomplished from selectively protected methyl l-arabinofuranosides. 2(3)-Deoxy-l-pentofuranosides, including 2-deoxy-l-ribofuranoside, and their 5-O-blocked derivatives were prepared by stereoselective reductions of 2,3-anhydro-l-furanosides with l-Selectride.
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