Glyculosonic acids reactions

Chain-extension reactions constitute a more widely used approach. Thus, the cyanohydrin synthesis followed by base-catalyzed cyclization and /1-elimination to iminolactones, which then undergo stepwise hydrolysis, affords 3-deoxy-2-glyculosonic acids.313 The overall yield of this reaction is low. Paerels314 used this method to prepare the first crystalline members of this group, namely 3-deoxy-D-m //iro-hex-2-ulosopyranosonic acid (2-keto-3-deoxy-D-gluconic acid, KDG, 119), and the L isomer, starting from D-ribose and L-arabinose, respectively. The synthesis of 119 is illustrated in Scheme 10. 

H. S. Isbell, H. L. Frush, and Z. Orhanovic, Oxidation of sodium salts of alduronic and glyculosonic acids by sodium peroxide, Carbohydr. Res., 36 (1974) 283-291 Oxidation of certain cyclic carbonyl compounds with alkaline hydrogen peroxide, ibid., 43 (1975) 93-100 H. S. Isbell, Concurrent oxidation and reduction reactions of cyclohexanehexone, rhodizonic acid, and tetrahydroxy-l,4-benzoquinone with hydrogen peroxide, ibid., 39 (1975) C4-C7. 

Glycosyl halides, reaction with ethyl potassium dithiocarbonates, 111 —, poly-O-acetyl-, solvolysis of, 39 Glyculosonic acids, 3-deoxy-, 253, 254 Glyoxal, bis(phenylhydrazone), 81 Guanosine, 5-(fucosyl dihydrogen pyrophosphate), 205 5-phosphate, 227 trihydrogen pyrophosphate, 205 —, 2-deoxy-, 5-triphosphate, 231 Guaran, 71, 75... 

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