The fate of the methanesulfonyloxy group on reduction with LAH

Éva Bozó, Sándor Boros, János Kuszmann, Eszter Gács-Baitz

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

Reduction of 1,6:2,5-dianhydro-3,4-di-O-methanesulfonyl-1-thio-D- glucitol with LAH afforded the corresponding 3,4-dihydroxy compound in a yield of 51% and six by-products were isolated after acetylation. Three differed from the original molecule only in the substituents, which were AcO at C-3 and H, CH3S and CH3SCH2S at C-4, respectively. The other compounds had a rearranged skeleton and were 1,4:2,5-dianhydro-1-thio-D-galactitol derivatives, containing the AcO group at C-3 and the aforementioned three substituents attached to C-6. A mechanism is suggested for the rearrangement, and for the formation of the substituents including the fate of the methanesulfonyloxy groups on reduction with LAH which is generally applicable to any mesyloxy derivative.

Original languageEnglish
Pages (from-to)8095-8102
Number of pages8
JournalTetrahedron
Volume55
Issue number26
DOIs
Publication statusPublished - Jun 25 1999

Keywords

  • Mechanisms
  • Rearrangements
  • Reduction
  • Stereochemistry
  • Sulfonic acids and derivatives

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint Dive into the research topics of 'The fate of the methanesulfonyloxy group on reduction with LAH'. Together they form a unique fingerprint.

  • Cite this