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- W2483670798 abstract "Our approach to achieve a partial synthesis of methanopterin (1) started from 6-acetyl-O4-isopropyl-7-methylpterin (20) which was obtained either by condensation from 6-isopropoxypyrimidine-2,4,5-triamine (19) and pentane-2,3,4-trione (6) or from 6-isopropoxy-5-nitrosopyrimidine-2,4-diamine (21) and pentane-2,4-dione (=acetylacetone; 22) (Scheme 2). NaBH4 reduction of 20 led to 6-(1-hydroxyethyl)-O4-isopropyl-7-methylpterin (23) which was converted into the corresponding 6-(1-chloroethyl) and 6-(1-bromoethyl) derivatives 24 and 25. A series of nucleophilic displacement reactions in the side chain and at position 4 were performed as model reactions to give 26–29, 32–35, and 39–41. Hydrolysis of the substituents at C(4) led to the corresponding pterin derivatives 30, 31, 36–38, and 42. Analogously, 25 reacted with 1-(4-aminophenyl)-1-deoxy-2,3: 4,5-di-O-isopropylidene-D-ribitol (43), prepared from N-(4-bromophenyl)benzamide (47) via 49 and 50 to give 1-{4-{{1-[2-amino-7-methyl-4-(1-methylethoxy)pteridin-6-yl]ethyl}amino}phenyl}-1-deoxy-D-ribitol (44) in 62% yield (Scheme 3). Acid cleavage of the isopropylidene groups at room temperature led to 45 and on boiling to 1-{4-{[1-(2-amino-3,4-dihydro-7-methyl-4-oxopteridin-6-yl)ethyl]amino}phenyl}-1-deoxy-D-ribitol (46). The next step, however, attachment of the ribofuranosyl moiety with 55 or 56 to the terminal 1-deoxy-D-ribitol OH group could not been achieved. The second component, bis(4-nitrobenzyl) 2-{[(2-cyanoethoxy)(diisopropylamino)phosphino]oxy}pentanedioate (61), to built-up methanopterin (1) was synthesized from 2-hydroxypentanedioic acid (59) and worked well in another model reaction on phosphitylation with N6-benzoyl-2′,3′-O-isopropylideneadenosine and oxidation to give 62 (Scheme 6)." @default.
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- W2483670798 date "2007-10-01" @default.
- W2483670798 modified "2023-10-17" @default.
- W2483670798 title "Pteridines. Part CXVIII" @default.
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- W2483670798 doi "https://doi.org/10.1002/hlca.200790195" @default.
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