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*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

2 Citations (Scopus)
61 Downloads (Pure)

Abstract

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.

Original languageEnglish
Pages (from-to)5622-5626
Number of pages5
JournalOrganic letters
Volume22
Issue number14
DOIs
Publication statusPublished - 17-Jul-2020

Keywords

  • BRANCHED-CHAIN SUGARS
  • REGIOSELECTIVE OXIDATION
  • EVALOSE

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