cas 15837-08-8, 2,6-DIHYDROXY-3,9-DIMETHYLPURINE | Articles data ｜lookchem

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15837-08-8

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Purines XIV. [1]. Reactivity of 8-Bromo-3,9-dimethylxanthine Towards Some Nucleophilic Reagents
The reactivity of 8-bromo-3,9-dimethylxanthine (6) towards a variety of nucleophilic reagents has been investigated. Nucleophilic displacements take place easily with aliphatic mercaptans and aliphatic alcohols, whereas aliphatic amines required more severe conditions. Prolonged heating of 6 with amines causes a new type of rearrangement from 3,9- to 3,7-dimethylxanthines due to a 1,3-sigmatropic shift of the N(9)-methyl group.
Youssef, Shaker,Pfleiderer, Wolfgang
p. 949 - 954
(1998)
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3-METHYLXANTHOSINE: SYNTHESIS AND ACIDIC HYDROLYSIS OF THE GLYCOSYL BOND
An improved synthesis of 3,9-dimethylxanthine (2a) was achieved via the reaction of 1-methyl-5-(methylamino)-imidazole-4-carboxamide (3a) with EtOCOCl in acetate buffer (pH 5) followed by treatment with aqueous NaOH.This method was successfully applied to the synthesis of 3-methylxanthosine (2b), whose N-glycosidic bond proved to be remarkably sensitive to acidic hydrolysis: 2b underwent hydrolysis at a rate more than 1000 times faster than that of xanthosine (10) in 1.0N aqueous HCl at 25 deg C.Keywords: 3-methylxanthosine synthesis; 3,9-disubstituted xanthine; imidazolylcarbamic acid ester; base-catalyzed cyclization; amide carbamate cyclization; N-glycosidic bond hydrolysis; carbamate cis-trans isomerism; NMR; kinetic study
Itaya, Taisuke,Harada, Tsunehiro
p. 1235 - 1238
(2007/10/02)

SYNTHESIS OF 3,9-DIALKYLGUANINES AND THEIR CONVERSION INTO 3-ALKYLWYES, MODELS FOR THE FLUORESCENT NUCLEOSIDES FROM PHENYLALANINE TRANSFER RIBONUCLEIC ACIDS
Synthesis of 3,9-dialkylguanines 5 has been accomplished by N-cyanation of 1-alkyl-5-(alkylamino)imidazole-4-carboxamides 3 followed by base-catalysed cyclisation.Cyclocondensation of 9-alkyl-3-methylguanines 5a, d, f with MeCOCH2Br gave 3-alkylwyes 6, model compounds of the most probable structure for wyosine from Torulopsis utilis tRNAPhe.
Itaya, Taisuke,Ogawa, Kazuo
p. 1767 - 1774
(2007/10/02)

SYNTHESIS OF 3-METHYLXANTHOSINE
Treatment of 1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-5-(methylamino)imidazole-4-carboxamide (VIb) with EtOCOCl followed by cyclization with 1 N NaOH gave 3-methylxanthosine (Va).The glycosidic bond of Va underwent acid hydrolysis at a rate more than 1000 times greater than that of xanthosine.
Itaya, Taisuke,Harada, Tsunehiro
p. 687 - 690
(2007/10/02)

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Chemical Properties

Melting Point: ≥300 °C
Density: 1.6g/cm³
Refractive Index: 1.737
PKA: 10.48±0.20(Predicted)
BRN: 3679243
PSA: 72.68000
LogP: -1.03970

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