ChemInform Abstract: Pseudo‐Sugars. Part 30. Synthesis of Amino‐5a‐carba‐deoxyhexopyranoses from 2(3)‐Acetoxy‐5‐acetoxymethyl‐3(2)‐p‐toluenesulfonamido‐7‐ oxabicyclo(2.2.1)heptanes.

Abstract

Pseudo-Sugars.Part 30. Synthesis of Amino-5a-carbadeoxyhexopyranoses from 2(3)-Acetoxy-5-acetoxymethyl-3(2)p-toluenesulfonamido-7-oxabicyclo(2.2.1)heptanes.-cis-Hydroxyamination of unsaturated endo-acetate (I) under Sharpless conditions followed by acetylation of the positional isomers formed yields the acetates (IV) and (V). Cleavage of their 1,4-anhydro ring with HBr affords bromodeoxycyclitol derivatives which can be easily converted to the target amino-hexopyranoses (cf. (IX), (X)). Applying a similar sequence of reactions to the exo-acetate (XI) offers a convenient approach to the novel talopyranose tetraacetate (XII). -(OGAWA, S.; TSUNODA, H.; YOSHIKAWA, M.; UEMURA, M.; ORIHARA, M.; Liebigs Ann. Chem. (1992) 6, 629-636; Dep. Appl. Chem., Fac. Sci.