The Formation of Polyhydroxy-dialdehydes. II. d-Lyxo-trihydroxy-glutaric Dialdehyde and its Derivatives

Abstract

(1) Monoacetone-d-mannose was now obtained as colourless crystalline needles and its structure was established as 2,3-monoacetone-d-mannofuranose (III). Melting point, 80.5–82°. [α]D15=+4.5° (5 minutes)→−3.7° (40 hours) in water. And triaeetyl-monoacetone-d-mannose was ascertained to have the constitution (VI). (2) Bis-phenylhydrazone of d-lyxo-trihydroxy-glutarie dialdehyde was obtained as colourless needles, starting from 2,3-monoacetone-d-mannofuranose. Melting point, 168.5–169°. [α]D15=−72° in pyridine. Equilbrium rotation of d-lyxo-trihydroxy-glutaric dialdehyde was measured. [α]D15=+5° in water. Bis-p-nitrophenylhydrazone of d-lyxo-trihydroxyglutaric dialdehyde was obtained as orange-yellow leaflets. Melting point, 207–207.5°. Strontium salt of d-lyxo-trihydroxy-glutaric acid was obtained by oxidizing the dialdehyde with bromine in presence of strontium carbonate.