Related Experiment Video
Updated: Jan 16, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Structural Bias Effect On Azidation at C‑1 and C‑2 of Alkyl-3,6-anhydro‑d‑hexofuranosides: Synthetic Approach to
Ratul Hore1, Koushik Bit1, Rajatava Pan1
1Department of Chemistry, Ramakrishna Mission Residential College, Narendrapur, Kolkata 700103, India.
Abstract:
3,6-Anhydro hexofuranose sugars are the structural motif of natural product furanodictines A-B and sauropunols A-D, F, and H. Conversion of the 2-hydroxyl group of alkyl-3,6-anhydro-5-O-benzoyl-d-glucofuranosides to triflate intermediates followed by azidation reaction yielded 2-deoxy-2-azido derivatives when the substituents at C-1and C-2 are in cis relation; on the other hand, in the case of trans substituents, the products were α-glycosyl azide analogues. A similar reaction of butyl-3,6-anhydro-5-O-benzoyl- d-mannofuranosides, obtained from the corresponding α- or β-d-glucofuranoside through appropriate oxidation and reduction reactions, yielded only 2-deoxy-2-azido products. We report here in a synthetic approach to 2-substituted sauropunols, furanodictines A-B, and related analogues, along with 1,4-disubstituted 1,2,3-triazolyl glycoconjugates and N-glycosyl amide starting from d-glucose derived precursors.
Related Concept Videos
Preparation of 1° Amines: Azide Synthesis
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
Aryldiazonium Salts to Azo Dyes: Diazo Coupling
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration
Basicity of Heterocyclic Aromatic Amines
Nucleophilic Aromatic Substitution: Elimination–Addition

