Pterins. Part 2. Stereochemistry of catalytic reduction of 6-methyl- and 6,7-dimethyl-pterin and of 2,4-diamino-6-methylpteridine
- 1 January 1977
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 23,p. 2529-2536
- https://doi.org/10.1039/p19770002529
Abstract
Catalytic addition of two molecules of hydrogen to 7-deuterio-6-trideuteriomethylpterin yields a 0.8 : 1 mixture of cis- and trans-7-deuterio-6-trideuteriomethyl-5,6,7,3-tetrahydropterin. Similar reduction of 2,4-diamino-7-deuterio-6-(partial)trideuteriomethylpteridine gives a 1 : 1 mixture of cis- and trans-2,4-diamino-7-deuterio-6-(partial)trideuteriomethyl-5,6,7,8-tetrahydropteridine. Catalytic reduction of 6,7-dimethyl-and 6,7-bis(trideuterio-methyl)pterin, on the other hand, is stereospecific and forms only the cis-5,6,7,8-tetrahydro-derivatives. Reduction of 6,7-dimethylpterin with sodium in ethanol provides a 1 : 1 mixture of cis- and trans-6,7-dimethyl-5,6,7,8-tetra-hydropterin. The stereochemistry of these products was deduced from 1H n.m.r. spectroscopy.Keywords
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