Stereoselective Protection-Free Modification of 3-Keto-saccharides

Nittert Marinus, Nabil Tahiri, Margherita Duca, L M C Marc Mouthaan, Simona Bianca, Marco van den Noort, Bert Poolman, Martin D Witte, Adriaan J Minnaard*

*Bijbehorende auteur voor dit werk

OnderzoeksoutputAcademicpeer review

15 Citaten (Scopus)
130 Downloads (Pure)

Samenvatting

Unprotected 3-keto-saccharides have become readily accessible via site-selective oxidation, but their protection-free functionalization is relatively unexplored. Here we show that protecting groups are obsolete in a variety of stereoselective modifications of our model substrate methyl α-glucopyranoside. This allows the preparation of rare sugars and the installation of click handles and reactive groups. To showcase the applicability of the methodology, maltoheptaose has been converted into a chemical probe, and the rare sugar evalose has been synthesized.

Originele taal-2English
Pagina's (van-tot)5622-5626
Aantal pagina's5
TijdschriftOrganic letters
Volume22
Nummer van het tijdschrift14
DOI's
StatusPublished - 17-jul.-2020

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