Skip to main content
placeholder image

Synthesis of thiazole analogues of the immunosuppressive agent (1R,25,3A)-2-acetyl-4(5)-(1,2,3,4-tetrahydroxybutyl)imidazole

Journal Article


Abstract


  • The synthesis of four of the diastereoisomers of 2-acetyl-5-(l ,2,3,4-tetrahydroxybutyl)thiazole and two of the diastereoisomers of 2-acetyl-5-( 1,2,3,4,5-pentahydroxypentyl)thiazole and 2-acetyl-4-( 1,2,3,4,5-pentahydroxypentyl)thiazole are reported. These syntheses involve the condensation of 5- or 4-metallated 2-( 1,1 -dimethoxyethyl)thiazoles with 2,3-O-isopropylidene-D-erythrono-l,4-lactone or 5-O-(tert-butyldimethylsilyl)-2,3-O-isopropylideneD-ribonolactone followed by reductive ring-opening of the resulting lactols. The stereochemistries and structures of some key compounds have been determined by single crystal X-ray structural analysis.

Publication Date


  • 1999

Citation


  • Jeoffreys, G. R., Ung, A. T., Pyne, S. G., Skelton, B. W., & White, A. H. (1999). Synthesis of thiazole analogues of the immunosuppressive agent (1R,25,3A)-2-acetyl-4(5)-(1,2,3,4-tetrahydroxybutyl)imidazole. Journal of the Chemical Society - Perkin Transactions 1, (16), 2281-2291. doi:10.1039/a903675j

Scopus Eid


  • 2-s2.0-33746388302

Web Of Science Accession Number


Start Page


  • 2281

End Page


  • 2291

Issue


  • 16

Abstract


  • The synthesis of four of the diastereoisomers of 2-acetyl-5-(l ,2,3,4-tetrahydroxybutyl)thiazole and two of the diastereoisomers of 2-acetyl-5-( 1,2,3,4,5-pentahydroxypentyl)thiazole and 2-acetyl-4-( 1,2,3,4,5-pentahydroxypentyl)thiazole are reported. These syntheses involve the condensation of 5- or 4-metallated 2-( 1,1 -dimethoxyethyl)thiazoles with 2,3-O-isopropylidene-D-erythrono-l,4-lactone or 5-O-(tert-butyldimethylsilyl)-2,3-O-isopropylideneD-ribonolactone followed by reductive ring-opening of the resulting lactols. The stereochemistries and structures of some key compounds have been determined by single crystal X-ray structural analysis.

Publication Date


  • 1999

Citation


  • Jeoffreys, G. R., Ung, A. T., Pyne, S. G., Skelton, B. W., & White, A. H. (1999). Synthesis of thiazole analogues of the immunosuppressive agent (1R,25,3A)-2-acetyl-4(5)-(1,2,3,4-tetrahydroxybutyl)imidazole. Journal of the Chemical Society - Perkin Transactions 1, (16), 2281-2291. doi:10.1039/a903675j

Scopus Eid


  • 2-s2.0-33746388302

Web Of Science Accession Number


Start Page


  • 2281

End Page


  • 2291

Issue


  • 16