NUCLEOPHILIC REACTIONS IN CARBOHYDRATE CHEMISTRY.
Abstract
The powerfully nucleophilic azide ion was used in the preparation of epimino-, diamino-, and aminomercapto-sugar derivatives. Methyl 4,6-0-benzylidene-2, 3-dideoxy 2, 3-epimino-alpha-D-alloside, and the corresponding mannoside were prepared in excellent yield from the corresponding manno- and allo-epoxides. Methyl 3-azido-3-deoxy-alpha-Daltroside 2-toluene-p-sulfonate and the corresponding 2-azido altroside 3-toluene-p-sulfonate were prepared by acid hydrolysis of 4,6-0-benzylidene compounds. Treatment of these compounds with methanolic hydrazine-hydrate-Raney nickel bave the two 4,6-hydroxy epimines. Treatment of methyl 2, 3-anhydro-4, 6-0-benzylidene-alpha-Dmannoside with thiourea in boiling ethanol gave the 2, 3-epithio-alloside in one step. (Author)
Document Details
- Document Type
- Technical Report
- Publication Date
- Oct 31, 1963
- Accession Number
- AD0429749
Entities
People
- D. P. Murphy
Organizations
- University of Leicester