Beilstein J. Org. Chem.2011,7, 369–377, doi:10.3762/bjoc.7.47
–alkyne cycloaddition (CuAAC) reaction [33][34].
Results and Discussion
Since their introduction by Palcic and co-workers [35], hydrophobic alkyl glycosides have proven to be valuable derivatives for enzymatic assays, as their lipophilic nature allows easy product isolation by either reversed-phase
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Graphical Abstract
Scheme 1:
Indicative topology model for the biosynthesis of the glycophospholipids PIMs, LM and LAM in mycoba...
Beilstein J. Org. Chem.2010,6, No. 58, doi:10.3762/bjoc.6.58
cycloaddition of azide and alkynes, CuAAC) constitutes another interesting approach. The versatile nature of this reaction has led to a tremendous amount of work, mainly due to the quantitative yields and the possibility of carrying out the synthesis in either organic solvents or water. Moreover, since various
), 26.00–26.07 (C-6, C-8), 18.57 (C-3).
Coupling of azido functionalized carbohydrates by CuAAC
The dry copolymer (100 mg, containing approximately 75 mg, 0.68 mmol of propargyl acrylate) and compound 4 (229 mg, 1.0 equiv vs propargyl acrylate) were dissolved in a 1:1 mixture of THF and water (4 mL) at
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Graphical Abstract
Figure 1:
Preparation of the 8-azido-3,6-dioxaoctyl α-D-mannopyranoside.