PURIFICATION OF 2,3,6,7,10,11-HEXAMETHOXYTRIPHENYLENE AND PREPARATIONOF HEXAKISCARBONYLMETHYL AND HEXAKISCYANOMETHYL DERIVATIVES OF 2,3,6,7,10,11-HEXAHYDROXYTRIPHENYLENE

2,3,6,7,10,11-Hexamethoxytriphenylene (1) was subjected to an improved purification procedure and demethylated to give 2,3,6,7,10,11-hexahyd roxytriphenylene (2) as the relatively stable trihydrate. Compound 2 w as alkylated with reactive halogen reagents giving 2,3,6,7,10,11-hexak is(cyanomethyl)triphenylene (3), hexakis(N,N-diethylcarbamoylmethyloxy )triphenylene (4) and 10,11-hexakis(ethoxycarbonylmethyloxy)triphenyle ne (5). Reduction of 4 gave ,7,10,11-hexakis(diethylaminoethyloxy)trip henylene (6) and reduction of 5 followed by acetylation gave 3,6,7,10, 11-hexakis(acetyloxyethyloxy)triphenylene (7). Hydrolysis of 5 gave ,3 ,6,7,10,11-hexakis(carboxymethyloxy)triphenylene (8). Compound 8 could be converted to its corresponding active N-hydroxysuccinimide ester ( 9) by the DCC method. Compound 9 was found to be a versatile core mole cule that could be coupled with glycine-t-butyl ester, L-phenylalanine and L-phenylalanine-t-butyl ester giving compounds 10, 11 and 12.