73978-45-7Relevant articles and documents
Pteridines, LXIX. Synthesis and Reactivity of 2,4-Diamino-6-(hydroxymethyl)pteridine
Boyle, Peter H.,Pfleiderer, Wolfgang
, p. 1514 - 1523 (2007/10/02)
Condensation of 2,4,5,6-tetraaminopyridine (2) with 1,3-dihydroxyacetone in the presence of gaseous oxygen, rather than air, resulted in 2,4-diamino-6-(hydroxymethyl)pteridine (3) virtually uncontaminated with 2,4-diamino-6-methylpteridine (4).Acetylation of 3 led to 6-acetoxymethyl-2,4-bis(acetylamino)pteridine (5) which turned out to be very labile forming various di- and monoacetyl derivatives (6, 7, 9, 10) on mild hydrolytic conditions.Their structures are proven by physical-chemical means.Silylation of 3 to the tris(trimethylsilyl) derivative 11 followed by treatment with 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (12) and 1,2,3,4,6-penta-O-acetyl-β-D-glucopyranose (15), respectively, in the presence of boron trifluoride,led to selective formation of the corresponding acylated 2,4-diamino-6-pteridinyl O-glycosides 13 and 15, respectively.Deacylations of these afforded the free O-glycosides 14 and 17 which have been characterized by UV- and NMR spectra as well as pKa measurements.
