A stereoselective synthesis of xylitol

David Holland*, J. Fraser Stoddart

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

5 Scopus citations

Abstract

Rel-(2S, 3R, 4R)- (6) and rel-(2R,3R,4R)- (7) 1,2,5-triacetoxy-3,4-epoxypentanes have been obtained in seven steps starting from cyclopentadiene. Both diastereoisomers afford xylitol pentaacetate (8) selectively upon epoxide cleavage with acetate ion. In the case of (6), rel-(1s,3R,4r,5S)-3,-bisacetoxymethyl-1-methyl-2,6,7-trioxabicyclo- [2.2.1]heptane (11) has been isolated and characterised as an intermediate in the reaction.

Original languageEnglish (US)
Pages (from-to)5367-5370
Number of pages4
JournalTetrahedron Letters
Volume23
Issue number50
DOIs
StatePublished - 1982

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint Dive into the research topics of 'A stereoselective synthesis of xylitol'. Together they form a unique fingerprint.

Cite this