II. CHEMISTRY 



319 



H3C 



H3C 



H3C 



CH20H 



I 



HOCH 



I 

 HOCH 



I 

 CO 



I 



CH2 



I 



NH 



Ft + Hi 

 alkaline 

 solution 



\/\/ 



H 



H3C 



/S/ 



H3C 



CH20H 



I 



HOCH 



I 

 HOCH 



I 

 HOCH 



CH2 



NH 



III 



/V 



H3C 



reaction product is converted into tetraacetylribonic acid by treatment 

 with nitrous acid, which then is reacted with PCI5 to form the acid chloride. 

 This is reduced to give tetraacetyl-D-ribose, palladium supported on BaS04 

 being used as a catalyst. Hydrogenation of tetraacetyl-D-ribose in the pres- 

 ence of o-4-xyndine, with Raney nickel or platinum as catalyst, yields 

 tetraacetyl-l-D-ribityl-o-4-xylidine, which finally is coupled wdth a phenyl- 

 diazonium salt. A similar method uses tetrabutyril-D-ribonamide as a start- 

 ing material."" 



A somewhat different method starts mth D-ribonolactone, prepared from 

 D-arabonic acid via n-ribonic acid.''' The lactone is reacted Avith xyhdine, 



^» Merck and Co., U. S. Pat. 2,424,341 (Sept. 22, 1947) [C.^. 42, 211 (1948)]. 



" M. Tishler, X. L. Wendler, K. Ladenburg, and J. W. Wellman, J . Am. Chem. Soc. 

 66, 1328 (1944); Merck and Co., U. S. Put. 2,420,210 (May 6, 1947) [C.A. 41, 5548 

 (1947)]; Hoffman-La Roche Inc., U. S. Pats. 2,438,881, 2,438,883 (March 3, 1948) 

 [C.A. 42,5048 (1948)]. 



