抄録
Type 2 telomers (n=1, 2) of vinylene carbonate 1 with polyhalomethanes, carbon tetrachloride and chloroform, were transformed to pentoses (triose) by new route involving two-step conversion of trichloromethyl groups into aldehydes, and tetroses and hexoses by smooth cyanation followed by reductive hydrolysis of trichloromethyls in analogous treatment described for pentoses. Thus DL-arabinose and DL-xylose were prepared in 44% (and 32%) and 43% (and 38%) yields from 5-chloro-5'-trichloromethyl-[4, 4'-bi-1, 3-dioxolane]-2, 2'-dione, 3 and 4 (and 5-trichloromethyl-[4, 4'-bi-1, 3-dioxolane]-2, 2'-dione, 5 and 6), respectively, providing the unamiguous stereochemistry of the n=2 telomers 3 and 4 (and 5 and 6) as trans-"syn"-trans and trans-"anti"-trans configurations. 4-Chloro-5-trichloromethyl-1, 3-dioxolan-2-one 13 gave DL-glyceraldehyde, DL-threose and DL-erythrose. DL-Galactose and DL-altrose, and DL-idose and DL-glucose were obtained from the syn form 3, and the anti form 4, respectively.