Value-added carbohydrate building blocks by regioselective O-alkylation of C-glucosyl compounds
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....
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Published in | Carbohydrate research Vol. 477; pp. 1 - 10 |
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Main Authors | , , |
Format | Journal Article |
Language | English |
Published |
OXFORD
Elsevier Ltd
15.05.2019
Elsevier |
Subjects | |
Online Access | Get full text |
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Summary: | 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.
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•Efficient synthesis of C-azidopropylglucopyranosides.•Regioselective alkylation of C-glucopyranosides.•Access to value-added C-glycosyl derivatives. |
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Bibliography: | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
ISSN: | 0008-6215 1873-426X 0008-6215 |
DOI: | 10.1016/j.carres.2019.03.008 |