A NOVEL CARBOHYDRATE REACTION
Abstract
Under support from the Sugar Research Foundation, plastic materials from sugar were prepared. Patents for new polymers and an effective bonding adhesive for glass have been applied for. The mesylation of methyl a-D-glucopyranoside was examined. From the reaction of methyl a-Dglucopyranoside with 2.2 moles of mesyl chloride, a crystalline compound was isolated in 51% yield. Its str cture was proved to be methyl 2,6-di-O esyl-a-D-glucopyranoside by a three step synthesis of 3,4-di-O-methyl-D-glucose in a yield of approximately 25%, a considerable improvement on previous yntheses. Upon investigation of an unexpected by-product the direct nucleophilic displacement of a primary mesyloxy group by a methoxide ion was observed, a reaction which does not appear to have been noted previously in the carbohydrate field. In preliminary tests against the Dunning leukemia tumor, methyl 2,6-di-O-mesyl-a-D-glucoside showed activity. This compound is also a key substance in the synthesis of a potential radiation protective material. (Author)
Document Details
- Document Type
- Technical Report
- Publication Date
- Dec 01, 1962
- Accession Number
- AD0286065
Entities
People
- A.k. Mitra
- Derek H. Ball
- Louis Jr. Long
Organizations
- Army Research Office