Value-added carbohydrate building blocks by regioselective O-alkylation of C-glucosyl compounds

• Published in: Carbohydrate research Vol. 477; pp. 1 - 10
• Main Authors: Vucko, Timothé, Pellegrini Moïse, Nadia, Lamandé-Langle, Sandrine
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 15.05.2019; Elsevier
• Subjects: 1,2-trans-diol; Biochemistry & Molecular Biology; C-glycoside; Chemical Sciences; Chemistry; Chemistry, Applied; Chemistry, Organic; Life Sciences & Biomedicine; Physical Sciences; Regioselective alkylation; Science & Technology; 1,2-trans-diol; C-glycoside; Regioselective alkylation; DIOLS; POLYOLS; ACYLATION; BENZYLATION; ACETALS; IRON; CATALYST; DERIVATIVES; ORGANOTIN
• ISSN: 0008-6215; 1873-426X; 0008-6215
• DOI: 10.1016/j.carres.2019.03.008

Functionalized carbohydrates and especially functionalized C-glycosides are useful intermediates for the synthesis of complex carbohydrates of interest. In this paper, we describe the synthesis of C-azidopropylglucopyranosides and give a full account of their regioselective acylation and alkylation. Alkylation of these C-glucosyl compounds containing 1,2-trans-diol, namely 2- and 3-OH were first optimized with benzyl bromide. The reaction has then been extended to various electrophiles thus providing 3-O-substituted C-glucosyl compounds. These results are one of the first examples of regioselective alkylation with functionalized electrophiles on glycosyl compounds featuring a trans-vicinal diol. Furthermore, we describe some results obtained during regioselective deprotection of 4,6-O-benzylidene protecting group. This work opens the way to the synthesis of complex carbohydrate derivatives. [Display omitted] •Efficient synthesis of C-azidopropylglucopyranosides.•Regioselective alkylation of C-glucopyranosides.•Access to value-added C-glycosyl derivatives.