Search

A novel synthetic approach is described to incorporate one more carbon atom at C-2 position of phospholane oxides as homologated allylic alcohol by treatment of erythro -2,3-epoxy-3-methylphospholane 1-oxides with excess of dimethylsulfonium methylide.

Several new classes of deoxy phospha sugar derivatives, analogs of normal sugar derivatives, were conveniently synthesized using 1‐methoxy‐2‐phospholene 1‐oxide as a starting material. All compounds were structurally characterized by their spectral data, and stereochemistry was determined by spectral and X‐ray crystallographic analyses.

An efficient method is described in the synthesis of several novel deoxy phospha sugar pyrimidine nucleosides in racemic form, analogs of normal sugar nucleosides, in high yields by treatment of (±)-2-aminophospholane 1-oxide with several, α-cyano-, -acetyl-, -ethoxycarbonyl-β-ethoxy-N-ethoxycarbonylacrylamides.

A convenient and facile chemo- and regioselective oxidation of the allylic methylene group in a 2-phospholene ring system afforded the novel carbonyl derivatives of 2-phospholenes (2a–i). The method gives high conversion and selectivity in the formation of allylic ketones. The advantages of this oxidation method in such a five-membered pseudo sugar 2-phospholene ring are mentioned, and the oxidation is examined on several substituted 2-phospholenes (1a–i). © 2003 Wiley Periodicals, Inc. Heteroatom Chem 14:320–325, 2003; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.10154

A convenient synthetic approach is established to prepare a new class of 1- l -α-amino acid derivatives of phospholene oxides by amination of (±)-1-chloro-2-phospholene-1-oxides with several optically pure l -α-amino acid esters. All compounds obtained as a diastereomeric mixture in good to high yields. The two diastereomers were successfully separated by column chromatography and structurally identified by their spectral analyses.

A novel method has been developed for stereospecific conversion of 2-phospholene 1-oxides into their corresponding 2,3-epoxides in high yields using sodium peroxide as a reagent.

Several new classes of deoxy phospha sugar derivatives, analogs of normal sugar derivatives, were conveniently synthesized using 1‐methoxy‐2‐phospholene 1‐oxide as a starting material. All compounds were structurally characterized by their spectral data, and stereochemistry was determined by spectral and X‐ray crystallographic analyses.

A novel and facile synthetic method is described in the synthesis of several deoxy phospha sugar–sugar disaccharides, analogs of normal sugar disaccharides by treatment of (±)-2-bromo-3-methoxy-1-phenylphospholane 1-oxide with several pentose and hexose sugar acetonides.