The introduction of nitrogen, sulfur, and bromine substituents at C-4 of 2-acetamido-2-deoxy-D-mannopyranose has been readily achieved through opening of the 3,4-epoxide of 2-acetamido-1,6:3,4-dianhydro-2-deoxy-/3-D-talopyranose.
ChemInform Abstract: Synthesis of 4-Substituted-2-acetamido-2,4-dideoxy-mannopyranoses Using 1,6-Anhydro Sugar Chemistry.
β Scribed by R. THOMSON; M. VON ITZSTEIN
- Book ID
- 112025170
- Publisher
- John Wiley and Sons
- Year
- 2010
- Weight
- 29 KB
- Volume
- 27
- Category
- Article
- ISSN
- 0931-7597
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Synthesis and Glycosidic Coupling Reaction of Substituted 2,6-Dioxabicyclo[3.1.1]heptanes: 1,3-Anhydro-2-azido-4,6-di-O-benzyl-2deoxy-Ξ²-D-mannopyranose. -The title sugar (VII) is synthesized via the key intermediate (VI) starting from glucopyranoside (I). Anhydrosugar (VII) is quite reactive: ring-