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Dithiasuccinoyl (Dts) Amino-protecting Group used in Syntheses of 1,2-trans-Amino Sugar Glycosides

DOI: 10.1039/P19950000405

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 405 - 416 (1995)

Update date:2022-07-29

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Authors:

Meinjohanns, ErnstMeinjohanns, Ernst

Meldal, MortenMeldal, Morten

Paulsen, HansPaulsen, Hans

Bock, KlausBock, Klaus

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Article abstract of DOI:10.1039/P19950000405

Suitable protected D-glucosamine derivatives possessing the N-dithiasuccinoyl (N-Dts) protecting group of the amino function have been applied in a new alternative route to 1,2-trans-glycosylation.The O-(3,4,6-tri-O-acetyl-2-deoxy-2-dithiasuccinoylamino-β-D-glucopyranosyl) trichloroacetimidate 7 has been used to prepare corresponding β-glycosides in good yields promoted by Lewis acids.The N-dithiasuccinoyl protecting group was easy to remove by thiolysis using 2-sulfanylethanol or dithiothreitol or reductively using sodium boranuide, thus affording, after N-acetylation, the corresponding N-acetyl-β-D-glucosamine glycosides.It has been demonstrated that it is possible to reduce the Dts group in the presence of an azido group selectively by sodium boranuide or the Dts- and the azido group simultaneously by dithiothreitol, using diisopropylethylamine as a catalyst.The syntheses of the building blocks, Nα-Fmoc-Ser(Ac3-β-D-GlcNDts)-O-Pfp 10 and Nα-Fmoc-Thr(Ac3-β-D-GlcNDts)-OPfp 11, suitable for the solid-phase glycopeptide synthesis of β-O linked GlcNAc bearing glycopeptides are described.Furthermore, the preparation of the Nα-Fmoc-Asn4)-Ac2-β-D-GlcNAc>-OPfp building block 19, suitable for the solid-phase synthesis of N-glycopeptides, and the synthesis of the β-D-GlcNAc(1->6)-D-GalNAc disaccharide 27, a mucin core structure, demonstrate the use of N-dithiasuccinoyl protection in oligosaccharide synthesis.

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Product name:2-acetamido-3,6-di-O-benzoyl-2-deoxy-β-D-glucopyranosyl azide

Cas No:162894-87-3

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