Related Experiment Video
Updated: Jul 18, 2026

Synthesis of Indoxyl-glycosides for Detection of Glycosidase Activities
Published on: May 27, 2015
Synthesis and reactivity of nonstabilized diazo sugars
Michael S Alexander1, Derek Horton
1Department of Chemistry, American University, 4400 Massachusetts Avenue, NW, Washington, DC 20016, USA.
Abstract:
1,6-Anhydro-4-deoxy-4-diazo-2,3-O-isopropylidene-beta-D-lyxo-hexopyranose (4) is a stable crystalline compound readily accessible by an improved synthetic procedure. It has been used as a model for evaluating the reactivity of the diazo group, when not stabilized by an adjacent carbonyl function, in a rigid chiral matrix. A range of carbene-type, electrophile-promoted, and 1,3-dipolar reactions were evaluated, leading to 4,4'-alkene dimers, 4-deoxy-3-enose and related derivatives, 4,4-dihalo compounds, 4-spirocyclopropane derivatives, 4-spiropyrazole structures, and by skeletal rearrangement, branched-chain anhydropentose structures having a bicyclo[2.2.2] skeleton.
More Related Videos
07:06Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid
Published on: November 15, 2017
08:46Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides
Published on: July 26, 2018
Related Concept Videos
Aryldiazonium Salts to Azo Dyes: Diazo Coupling
Diazonium Group Substitution: –OH and –H
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism
Carboxylic Acids to Methylesters: Alkylation using Diazomethane
Biosynthesis of Polysaccharides