NITROGEN-CONTAINING CARBOHYDRATE DERIVATIVES .V. SYNTHESIS AND CONFIGURATIONAL DETERMINATION OF CARBOHYDRATE C-NITRO ALCOHOLS BY OPTICAL ROTATORY DISPERSION AND CIRCULAR DICHROISM

An epimeric pair 2-acetamido-1,2-dideoxy-1-nitro-D-glycero-D-talo-heptitol and 2-acetamido-1,2-dideoxy-1-nitro-D-glycero-D-galacto-heptitol, was synthesized from D-mannose. The absolute configuration at C-2 was based on the rules relating the signs of the Cotton effect of the o.r.d. curves and the c.d. maxima to the configuration at C-2 of the carbohydrate C-nitro alcohols. This assignment was confirmed by chemical degradation of 2-acetamido-1,2-dideoxy-1-nitro-D-glycero-D-talo-heptitol to D-serine. Another epimeric pair, 2-acetamido-1,2-dideoxy-1-nitro-D-glycero-L-manno-heptitol and 2-acetamido-1,2-dideoxy-1-nitro-D-glycero-L-gluco-heptitol, was synthesized, and the configurations at C-2, determined by optical methods, agreed with those established by chemical methods. © 1968.