Phase‐transfer catalysis in the <i>N</i>‐benzylation of adenine

Shinkai, I.; Zwan, Michael C. Vander; Hartner, Frederick W.; Reamer, Robert A.; Tull, Roger; Weinstock, Leonard M.

doi:10.1002/jhet.5570180138

Cited by 24 publications

(4 citation statements)

References 7 publications

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“…The major component, refined anisotropically, was present at 0.88 (1) and the minor component, C(94') and refined isotropically, was present at 0.12 (1). Η atoms were included for C(94).…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of 9-(3-butenyl)-adenine, C9H11N5

Crisp

Jiang

Tiekink

2000

Zeitschrift Für Kristallographie - New Crystal Structures

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“…The major component, refined anisotropically, was present at 0.88 (1) and the minor component, C(94') and refined isotropically, was present at 0.12 (1). Η atoms were included for C(94).…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of 9-(3-butenyl)-adenine, C9H11N5

Crisp

Jiang

Tiekink

2000

Zeitschrift Für Kristallographie - New Crystal Structures

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“…In support of this type of fragmentation, I -methylguanine (2Oc). and 1,3-dimcthyluracil (20a) lose CH,N from the molecular ion (30) 137 (12), 123 (9), 109 (10). 95 (13).…”

Section: El Mass Spectrometrymentioning

confidence: 99%

“…181 (loo), 161 ( 5 ) , 124 (6) 153 (10) 153 (-) 234 (5), 216 ( 8 ) , 181 (loo), 161 (6), 321 (5) 501 (12) 304 (9), 222 (5). 181 (100) 208 (-) 181 (90)' 161 (10).…”

Section: El Mass Spectrometryunclassified

Preparation and mass spectral characterization of pentafluorobenzyl derivatives of alkyl and hydroxyalkyl-nucleobase DNA adducts

Saha

Kresbach

Giese

et al. 1989

Biol. Mass Spectrom.

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Pentafluorobenzyl (PFBz) derivatives of the following nucleobases were prepared: cytosine, 5-methylcytosine, O2-methylcytosine, O2-ethylthymine, O4-ethylthymine, 5-hydroxymethyluracil, N6-methyladenine, O6-methylguanine, O6-hydroxyethylguanine and O6-hydroxyethylpurine. 13C nuclear magnetic resonance was diagnostic for O- versus N-attachment of the PFBz moiety: the resonance of the methylene carbon appeared in the range 29.15-42.13 ppm for NCH2C6F5, and 58.45-69.01 for OCH2C6F5. Considerable structural information was provided by mass spectrometry with ionization by electron impact. All of the derivatives were detected with high sensitivity and specificity by gas chromatography with detection by electron capture negative ion mass spectrometry, reflecting not only their chemical and physical stability, but also their strong tendency to form a structurally diagnostic anion, [M - PFBz]-, in high yield under these ionization conditions. PFBz derivatives are therefore attractive forms of alkyl-substituted nucleobases for analysis by mass spectrometry.

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“…The ylide intermediate formed during the Witting reaction is prone to hydrolysis but under PT conditions Israel Journalof Chemistry Vol.26 1985 pp.277-281 3-isomer. Under PT conditions, with a preformed Na or K salt [21] or with aqueous NaOH [39], the 9·alkyl isomer is prepared with a 80% yield [40] . M i NaBHc.. n + n + h…”

Section: Chemoselectivitymentioning

confidence: 99%