N-(9-Acetyl-6,9-dihydro-6-oxo-1H-purin-2-yl)acetamid

Bezeichnung:N-(9-Acetyl-6,9-dihydro-6-oxo-1H-purin-2-yl)acetamid

CAS-Nr3056-33-5

Englisch Name:N2,9-Diacetylguanine

CBNumberCB6183086

SummenformelC9H9N5O3

Molgewicht235.2

MOL-Datei3056-33-5.mol

Synonyma

N-(9-Acetyl-6,9-dihydro-6-oxo-1H-purin-2-yl)acetamid

N-(9-Acetyl-6,9-dihydro-6-oxo-1H-purin-2-yl)acetamid physikalisch-chemischer Eigenschaften

Schmelzpunkt	285 °C(lit.)
Dichte	1.67±0.1 g/cm3(Predicted)
storage temp.	Sealed in dry,Room Temperature
Löslichkeit	Aqueous Base (Slightly, Heated), DMSO (Slightly, Heated)
Aggregatzustand	Solid
pka	8.37±0.20(Predicted)
Farbe	White to Light Beige
InChI	InChI=1S/C9H9N5O3/c1-4(15)11-9-12-7-6(8(17)13-9)10-3-14(7)5(2)16/h3H,1-2H3,(H2,11,12,13,15,17)
InChIKey	GILZZWCROUGLIS-UHFFFAOYSA-N
SMILES	C(NC1NC(=O)C2=C(N=1)N(C(C)=O)C=N2)(=O)C
CAS Datenbank	3056-33-5(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	36/37/38
S-Sätze:	26-37/39-36
WGK Germany	3
HS Code	29339900

Gefahreninformationscode (GHS)

N2,9-Diacetylguanine Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S37/39:Bei der Arbeit geeignete Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
Beschreibung
N2,9-Diacetylguanine is a purine compound that can be prepared by acetylation of guanine with acetic anhydride. It can be used in many fields such as organic synthesis, biological research and pharmaceutical manufacturing. N2,9-Diacetylguanine can be prepared into 2-amino-6-halogenated purine under the action of two-step PEG-2000 phase transfer catalyst and TPPB phase transfer catalyst, and further through the corresponding CuX-catalyzed diazotization reaction, new 2-halogenated purine compounds can be efficiently synthesized^[2]. In addition, it can also be used as an intermediate for the antiviral drugs Ganciclovir and Aciclovir.
Chemische Eigenschaften
white or brownish crystalline powder
Verwenden
N2,9-Diacetylguanine (Acicclovir EP Impurity L) is used to synthesize acyclic analogues of deoxyguanosine.
Application
The alkylation of N2,N9- diacetylguanine (DAG) with 2-oxa-1, 4-butane-dioldiacetate to give N2-acetyl-9-{2-acetoxyethoxymethyl}- guanine (N9 isomer) and/or N2-acetyl-7-{2-acetoxyethoxymethyl}- guanine (N7 isomer) in exceptionally high regioselectivity[1].
Einzelnachweise
[1] Dharmendra Singh, Ashok Kumar, Mukesh J. Wani. “A Simple Solution to the Age Old Problem of Regioselective Functionalization of Guanine: First Practical Synthesis of Acyclic N9- and/or N7-Guanine Nucleosides Starting from N2,N9-Diacetylguanine.” The Journal of Organic Chemistry 64 13 (1999): 4665–4668.
[2] Y. HU. Synthesis of Some Biologically Active Halogenopurines[J]. Journal of the Korean Chemical Society-Daehan Hwahak Hoe Jee, 2010. DOI:10.5012/JKCS.2010.54.4.429.

N2,9-Diacetylguanine Upstream-Materialien And Downstream Produkte

N-(9-Acetyl-6,9-dihydro-6-oxo-1H-purin-2-yl)acetamid Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

3056-33-5, N2,9-Diacetylguanine Verwandte Suche:

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