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Improved preparation and synthetic uses of 3-deoxy-d-arabino-hexonolactone: an efficient synthesis ofLeptosphaerin

Authors
Journal
Carbohydrate Research
0008-6215
Publisher
Elsevier
Publication Date
Volume
315
Identifiers
DOI: 10.1016/s0008-6215(99)00007-5
Keywords
  • D-Glucono-1
  • 5-Lactone
  • 3-Deoxy-D-Arabino-Hexono-Lactone
  • 3-Deoxy-D-Arabino-Hexose
  • Enamine
  • Leptosphaerin
  • 2
  • 5-Anhydro-3-Deoxy-D-Ribo-Hexonic Acid

Abstract

Abstract Acetylation of d-glucono-1,5-lactone and subsequent treatment with triethylamine gave 2,4,6-tri- O-acetyl- d- erythro-hex-2-enono-1,5-lactone. Hydrogenation of the latter in the presence of palladium on carbon yielded 2,4,6-tri- O-acetyl-3-deoxy- d- arabino-hexono-1,5-lactone ( 5) in almost quantitative yield calculated from gluconolactone. Catalytic hydrogenation of 5 with platinum on carbon in the presence of triethylamine gave 2,4,6-tri- O-acetyl-3-deoxy- d- arabino-hexopyranose in quantitative yield. Deacetylation of 5 gave 3-deoxy- d- arabino-hexono-1,4-lactone, which was converted into 3-deoxy-5,6- O-isopropylidene-2- O-methanesulfonyl- d- arabino-hexono-1,4-lactone ( 10). The latter was converted into 2-acetamido-2,3-dideoxy- d- erythro-hex-2-enono-1,4-lactone ( Leptosphaerin). When 10 was boiled in water in the presence of acid, it gave a high yield of 2,5-anhydro-3-deoxy- d- ribo-hexonic acid.

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