Abstract
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.
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