2008
DOI: 10.1016/j.tet.2007.12.042
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Efficient total syntheses of natural pterin glycosides: limipterin and tepidopterin

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Cited by 12 publications
(9 citation statements)
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“…By use of the same procedures described in the literature, 14 compound 20 was converted into 23 in five steps: R f = 0.60 (1:9 MeOH-CHCl 3 ).…”
mentioning
confidence: 99%
“…By use of the same procedures described in the literature, 14 compound 20 was converted into 23 in five steps: R f = 0.60 (1:9 MeOH-CHCl 3 ).…”
mentioning
confidence: 99%
“…A marked improvement has been made to establish an efficient synthetic protocol to achieve completely regioselective 2′‐ O ‐glycosylation using a suitably 1′‐ O ‐protected (with p ‐methoxybenzyl (PMB)) biopterin derivative ( 10 ) as a key glycosyl acceptor (35, 36) (Scheme a). From a retrosynthetic analysis outlined in Scheme a compound 10 was thought best to be prepared by the condensation of 2,5,6‐triamino‐4‐hydroxypyrimidine ( 11 ) with 3‐ O ‐protected L ‐ erythro ‐pentos‐2‐ulose ( 12 ), which in turn would be derived from D ‐xylose via 3‐ O ‐protected 5‐deoxy‐ L ‐arabinose 13 involving C‐4 inversion and then C‐5 deoxygenation.…”
Section: Synthesis Of Limipterin (1d)mentioning
confidence: 99%
“…The 5‐deoxy‐4‐enofuranose derivative ( 14 ), prepared from D ‐xylose in four steps (37) was stereoselectively hydrogenated, followed by introduction of the PMB group to give the 5‐deoxy‐ L ‐arabinose derivative ( 15 ), which was then converted into 13 . Selective oxidation of the 2‐hydroxy group of 13 with cupric acetate provided the 3‐ O ‐PMB‐ L ‐ erythro ‐ pentos‐2‐ulose ( 12 ) (36).…”
Section: Synthesis Of Limipterin (1d)mentioning
confidence: 99%
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“…By contrast, the functional roles of pterin glycosides have remaind obscure, though some inhibitory activities against tyrosinase were reported for biopterin D-glucoside (2) (23). Despite a considerable interest from the viewpoint of their biological activities and functions as well as the structural proof of hitherto reported natural products, attempts at preparation of natural pterin glycosides have so far scarcely been made, except for our synthetic studies on biopterin and ciliapterin glycosides (24)(25)(26)(27)(28)(29)(30)(31). We describe herein an efficient synthesis of 3'-O-(β-D-glucopyranosyluronic acid)neopterin (6) as the first synthetic example of a natural neopterin glycoside.…”
Section: Introductionmentioning
confidence: 99%