Batsberg Pedersen, W.

Bechgaard, K.

Krebs, Frederik C

Schiødt, N.C.

English

Abstract: 2,3,6,7,10,11-Hexamethoxytriphenylene (1) was subjected to an improved purificationprocedure and demethylated to give 2,3,6,7,10,11- hexahydroxytriphenylene (2) as the relativelystable trihydrate. Compound 2 was alkylated with reactive halogen reagents giving 2,3,6,7,10,11- hexakis(cyanomethyl)triphenylene (3),2,3,6,7,10, 11-hexakis(N,N-diethylcarbamoylmethyloxy)triphenylene (4) and 2,3,6,7,10,11-hexakis ethoxycarbonyl- methyloxy)triphenylene (5). Reduction of 4 gave2,3,6,7,10,11-hexakis(diethylaminoethyloxy)triphenylene (6) and reduction of 5 followed by acetyla- tion gave ,3,6,7,10,11-hexakis acetyloxyethyloxy) triphenylene (7). Hydrolysis of 5 gave 2,3,6,7,10, 11-hexakis(carboxymethyloxy)triphenylene (8). Compound 8 could be converted to its coresponding active N-hydroxysuccinimide ester (9) by the DCC method. Compound 9 was found to be a versatile core molecule that could be coupled with glycine-t -butyl ester, L-phenylalanine and L-phenylalanine- t -butyl ester giving compounds 10, 11 and 12.2,3,6,7,10,11-Hexamethoxytriphenylene (1) was subjected to an improved purification procedure and demethylated to give 2,3,6,7,10,11-hexahydroxytriphenylene (2) as the relatively stable trihydrate. Compound 2 was alkylated with reactive halogen reagents giving 2,3,6,7,10,11-hexakis(cyanomethyl)triphenylene (3), 2,3,6,7,10,11-hexakis(N,N-diethylcarbamoylmethyloxy)triphenylene (4) and 2,3,6,7,10,11-hexakis(ethoxycarbonylmethyloxy)triphenylene (5). Reduction of 4 gave 2,3,6,7,10,11-hexakis(diethylaminoethyloxy)triphenylene (6) and reduction of 5 followed by acetylation gave 2,3,6,7,10,11-hexakis(acetyloxyethyloxy)triphenylene (7). Hydrolysis of 5 gave 2,3,6,7,10,11-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 molecule that could be coupled with glycine-t-butyl ester, L-phenylalanine and L-phenylalanine-t-butyl ester giving compounds 10, 11 and 12

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Purification of 2,3,6,7,10,11-hexamethoxytriphenylene and Preparation ofhexakiscarbonylmethyl and hexakiscyanomethyl derivatives of 2,3,6,7,10,11-hexahydroxytriphenylene - DTU Orbit (29/08/13)  Purification of 2,3,6,7,10,11-hexamethoxytriphenylene and Preparation of hexakiscarbonylmethyl and hexakiscyanomethylderivatives of 2,3,6,7,10,11-hexahydroxytriphenylene. / Krebs, Frederik C; Schiødt, N.C.; Batsberg Pedersen, W.;Bechgaard, K.In: SYNTHESIS-STUTTGART, No. 11, 1997, p. 1285-1290.Publication: Research - peer-review › Journal article – Annual report year: 1997  

Purification of 2,3,6,7,10,11-hexamethoxytriphenylene and Preparation of hexakiscarbonylmethyl and hexakiscyanomethyl derivatives of 2,3,6,7,10,11-hexahydroxytriphenylene

http://orbit.dtu.dk/en/publications/purification-of-23671011hexamethoxytriphenylene-and-preparation-of-hexakiscarbonylmethyl-and-hexakiscyanomethyl-derivatives-of-23671011hexahydroxytriphenylene(59a507b9-8abd-4de6-922b-60f315ea4883).html

Purification of 2,3,6,7,10,11-hexamethoxytriphenylene and Preparation of hexakiscarbonylmethyl and hexakiscyanomethyl derivatives of 2,3,6,7,10,11-hexahydroxytriphenylene

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