Anomeric spirocycles by solvent incorporation: Reactions of O-peracylated (glyculopyranose and glyculopyranosyl bromide)onamide derivatives with ketones

Research output: Article

7 Citations (Scopus)

Abstract

Reactions of O-peracetylated (α-d-galacto-heptulopyranosyl bromide)onamide and O-perbenzoylated (α-d-gluco-heptulopyranosyl bromide)onamide with ketones in the presence of silver(I) salt promoters gave the corresponding O-peracylated 1′,5′-anhydro-d-glycitol-spiro-[1′,5]-4-imino-2,2-disubstituted-1,3-dioxolanes. The d-galacto configured starting compounds furnished both spiro epimers, while the d-gluco counterparts yielded only configurationally inverted products. Under acidic conditions, O-perbenzoylated α-d-gluco-heptulopyranosonamide and ketones yielded the protected 1′,5′-anhydro-d-glucitol-spiro-[1′,5]-2,2-disubstituted-oxazolidin-4-ones, which were O-debenzoylated by the Zemplén protocol. These compounds had no inhibition against rabbit muscle glycogen phosphorlyase b.

Original languageEnglish
Pages (from-to)192-201
Number of pages10
JournalCarbohydrate Research
Volume403
DOIs
Publication statusPublished - febr. 11 2015

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Anomeric spirocycles by solvent incorporation: Reactions of O-peracylated (glyculopyranose and glyculopyranosyl bromide)onamide derivatives with ketones'. Together they form a unique fingerprint.

  • Cite this