Syntheses of branched non-1-ynitols by chemoselective addition of (trimethylsilyl)-propargylmagnesium bromide at the anomeric center of side chain halogeno functionalized carbohydrates

Sanjeev Kumar V. Vernekar, Paul Kipke, Hartmut Redlich

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

Abstract

A convenient method for the syntheses of non-1-ynitols 8a-8d, by chemoselective addition of (trimethylsilyl)-propargylmagnesium bromide at the anomeric center of a 1-unprotected sugar, in the presence of 3-C′-halide and 3-C′-silyl functions in the side chain is described. In addition, an efficient method for the synthesis of 3-C′-hydroxymethyl sugar 3 via the addition of C1 silyl Grignard reagents to ulose 1 and subsequent oxidation by the Fleming-Tamao method in excellent yields is reported. Also, a suitable acid-catalyzed isomerization of the 1,2-O-isopropylidene group to the 2,3-O-isopropylidene group (5a-5f), to get access to the anomeric center, in good to excellent yields has been depicted.

Original languageEnglish (US)
Pages (from-to)10-31
Number of pages22
JournalJournal of Carbohydrate Chemistry
Volume27
Issue number1
DOIs
StatePublished - Jan 2008

Keywords

  • Alkynes
  • Carbohydrates
  • Grignard reaction
  • Isomerizations

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