ChemicalBook CAS DataBase List 9-(2'-ACETOXYETHOXYMETHYL)-GUANINE

9-(2'-ACETOXYETHOXYMETHYL)-GUANINE synthesis

12synthesis methods

Product Name:9-(2'-ACETOXYETHOXYMETHYL)-GUANINE
CAS Number:102728-64-3
Molecular formula:C10H13N5O4
Molecular Weight:267.24

73-40-5 Synthesis

73-40-5
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$5.00/5g

59278-00-1 Synthesis

59278-00-1
173 suppliers
$10.00/5g

102728-64-3
114 suppliers
$65.00/25 mg

Yield: 58%

Reaction Conditions:

with ammonium sulfate;1,1,1,3,3,3-hexamethyl-disilazane in water;acetone

Steps:

3.A Preparation of Compounds of Formula (I) where R1 is Hydrogen
3A. Formula (4) where R² is Ethyl and R³ is Hydrogen A mixture of 10 gms (66 mmoles) of guanine, 50 ml of hexamethyldisilazane, and 0.4 gms (3 mmmol) of ammonium sulfate was heated to 115°-118° C. for 18 hours. The ammonia gas was removed as it was formed. After 18 hours of heating, a solution was formed indicating the completion of silylation. To this solution was added 15 gms (85 mmol) of 2-oxa-1,4-butanediol diacetate and 0.1 ml of trimethylsilyl triftriflate. The mixture was heated to 130° C. for a period of 4.5 hours. The solution was cooled to 50° C. and 10 ml of water dissolved in 100 ml of acetone was added. The mixture was heated to reflux and a precipitate was formed immediately. The mixture was cooled and the solid was collected by filtration to yield 10.1 g (58% yield) of 9-(2-acetoxyethoxy)methylguanine, with a 13:1 ratio of N-9 to N-7 isomer. Characteristic analytical data are as follows: ¹ H NMR (DMSO-d₆) δ1.90 (3H, singlet, --OAc), 3.58 (2H, multiplet, --OCH₂ --), 4.0 (2H, multiplet, --CH₂ OAc), 5.25 (2H, singlet, --NCH₂ O--), 6.5 (2H, br singlet, --NH₂), 7.75 (1H, singlet, --N=CH--N--).

References:

Syntex (U.S.A.) Inc. US5565565, 1996, A

59277-89-3 Synthesis