期刊
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
卷 9, 期 -, 页码 2395-2403出版社
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.9.276
关键词
continuous flow; flow chemistry: flow synthesis; glycoligands; multivalency; photochemistry; solid-phase synthesis; thiol-ene; thioglycosides
资金
- Max Planck Society
- German Research Foundation (DFG, Emmy Noether program) [HA5950/1-1]
We present the solid phase synthesis of carbohydrate-functionalized oligo(amidoamines) with different functionalization patterns utilizing a novel alphabet of six differently glycosylated building blocks. Highly efficient in flow conjugation of thioglycosides to a double-bond presenting diethylentriamine precursor is the key step to prepare these building blocks suitable for fully automated solid-phase synthesis. Introduction of the sugar ligands via functionalized building blocks rather than postfunctionalization of the oligomeric backbone allows for the straightforward synthesis of multivalent glycoligands with full control over monomer sequence and functionalization pattern. We demonstrate the potential of this building-block approach by synthesizing oligomers with different numbers and spacing of carbohydrates and also show the feasibility of heteromultivalent glycosylation patterns by combining building blocks presenting different mono- and disaccharides.
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