From d- to l-Monosaccharide Derivatives via Photodecarboxylation-Alkylation

I. C. Steven Wan, Martin D. Witte*, Adriaan J. Minnaard

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

24 Citations (Scopus)
176 Downloads (Pure)

Abstract

Photodecarboxylation-alkylation of conformationally locked monosaccharides leads to inversion of stereochemistry at C5. This allows the synthesis of l-sugars from their readily available d-counterparts. Via this strategy, methyl l-guloside was synthesized from methyl d-mannoside in 21% yield over six steps.

Original languageEnglish
Pages (from-to)7669-7673
Number of pages5
JournalOrganic letters
Volume21
Issue number18
DOIs
Publication statusPublished - 20-Sep-2019

Keywords

  • PHOTOREDOX
  • RADICALS
  • CONFORMATION
  • PEPTIDE
  • ESTERS

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