Studies of the synthesis of 1,2-cis-(cyclic carbamates) of α-d-aldopyranosylamines

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Abstract

Reaction of α-d-glucopyranosyl azide with triphenylphosphine and carbon dioxide gave 1-N,2-O-carbonyl-α-d-glycopyranosylamine (7) and its α-d-furanose analogue (1), and 1-N,3-O-carbonyl-α-d-allofuranosylamine (15) and its α-d-pyranose analogue (17). Similarly, α-d-xylopyranosyl azide gave 1-N,2-O-carbonyl-α-d-xylopyranosylamine (9) and its α-d-furanose analogue (3), and 1-N,3-O-carbonyl-α-d-ribopyranosylamine (19) and its β-d-xylopyranose analogue (21). The structures of the products and their acetylated derivatives were established by 1H and 13C NMR spectroscopy. 1-N,3-O-Carbonyl-β-d-xylopyranosylamine (21) was obtained from β-d-xylopyranosyl azide when spontaneous rearrangement of the 1,2-(cyclic carbamate) 5 into 21 occurred in water.

Original languageEnglish
Pages (from-to)95-106
Number of pages12
JournalCarbohydrate Research
Volume239
Issue numberC
DOIs
Publication statusPublished - Feb 1 1993

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ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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