ChemicalBook CAS DataBase List N-Benzoyladenosine

N-Benzoyladenosine synthesis

7synthesis methods

Product Name:N-Benzoyladenosine
CAS Number:4546-55-8
Molecular formula:C17H17N5O5
Molecular Weight:371.35

In the prior art, the method for preparing N-Benzoyladenosine generally adopts trimethylchlorosilane protection to obtain trimethyl protected adenosine, then benzoyl chloride is added for benzoylation. Finally, the protection is removed under the protection of ammonia water, then the benzoyl chloride is concentrated, the solvent is evaporated to dryness, and water is added for crystallization to afford N-Benzoyladenosine.

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98-88-4 Synthesis

98-88-4
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4546-55-8
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Yield:4546-55-8 90%

Reaction Conditions:

Stage #1:adenosine with pyridine;chloro-trimethyl-silane at 0; for 2 h;
Stage #2:benzoyl chloride at 25; for 14 h;

Steps:

1 benzoate 70
To a solution of33 (120g. 449 mmoi) in Py (1,0 L) is added TMSC1 (390g. 3.59 mol, 454 mL). After stirring at 0 °C for 2 hours, benzoyl chloride (316 g, 2.25 mol, 261 mL) is added dropwise and the mixture is stirred at 25 Q( for 14 hours before cooled to 0 °C. Water (240 mL) is then added and the mixture is stirred at 25 °C for 30 minutes before ammoniurn hydroxide (460 rnL) is added at 0 °C. After stirring for 2 hours, the mixture is concentrated to give 70 as a white solid (150 g. 90% yield)

References:

IMMUNE SENSOR, LLC;THE BOARD OF REGENTS OF THE UNIVERSITY OF TEXAS SYSTEM;ZHONG, Boyu;SUN, Lijun;WEI, Qi;DAI, Yuanwei;CHEN, Chuo;CHEN, Zhijian WO2017/161349, 2017, A1 Location in patent:Paragraph 0288

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98-88-4 Synthesis

98-88-4
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58-61-7 Synthesis