Synthetic Studies of Amino Acids by the Use of Copper(II) Complex. III. Syntheses of Several 2-Amino-2-deoxyaldonic Acids by the Use of Bisglycinato- and <i>N</i>-Pyruvylideneglycinatoaquocopper(II)

Abstract

Abstract A comparative study of the relative reactivity of bisglycinatocopper(II) and N-pyruvylideneglycinatoaquocopper(II) in a base-catalyzed condensation reaction with aldehydo sugar derivatives concluded that the latter complex is much more reactive than the former. This reaction was found to proceed with a considerably high stereoselectivity to afford blocked 2-amino-2-deoxyaldonic acids with a threo configurational relationship between C–2 and C–3, and between C–3 and C–4. The resultant products were converted to the corresponding free 2-amino-2-deoxyaldonic acids in good yields by deblocking them with Amberlite IR-12OB(H form).