2′,3′-Isopropylideneguanosine
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2′,3′-Isopropylideneguanosine
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CAS No:
362-76-5
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Formula:
C13H17N5O5
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Chemical Name:
2′,3′-Isopropylideneguanosine
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Synonyms:
Guanosine,2′,3′-O-(1-methylethylidene)-;Guanosine,2′,3′-O-isopropylidene-;Furo[3,4-d]-1,3-dioxole,guanosine deriv.;2′,3′-O-(1-Methylethylidene)guanosine;Isopropylideneguanosine;2′,3′-O-Isopropylideneguanosine;2′,3′-Isopropylideneguanosine;1803254-67-2
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CAS No:
Characteristics
133
-0.30720
White Crystalline Solid
1.9±0.1 g/cm3
299 °C (decomp)
647ºC at 760mmHg
345.1ºC
1.828
-20°C Freezer
2′,3′-Isopropylideneguanosine Use and Manufacturing
2-amino-9-(6-(hydroxymethyl)-2, 2-dimethyl-tetrahydrofuro[3, 4-d][l, 3]dioxoI-4- yl)-lH-purin-6(9H)-one (11). To a slurry of guanosine (0.25 g, 1.0 eq) (10) and acetone (15 mL) at room temperature was added 70percent HC1O4 (0.103 mL, 1.35 eq). The reaction was stirred for approximately 70 minutes, at which time it was clear and colorless. The reaction was then cooled to 0° C in an ice/water bath and concentrated NH4OH (0.167 mL, 1.41 eq) was added causing the formation of a milky white, gelatinous precipitate. The precipitate was collected on filter paper, resulting in a white papery solid that was dried at reduced pressure and ambient temperature for approximately 1 hour yielding 11 (0.262 g, 92percent).Step 1=2', 3'-Isopropylideneguanosine (E3a-I)To a suspension of guanosine (10 g, 35.31 mmol) in 600 ml of acetone was added 70percent perchloric acid (4.1 ml, 47.54 mmol). After 70 minutes, concentrated ammonium hydroxide (6.7 ml, 49.79 mmol) was added to the reaction mixture and cooled down with ice-water bath. The solid was filtered out and dried over vacuum, 9.5 g (83.2percent).To a solution of Guanosine (0, 5 g; 1, 76 mmoli) in 30 mL of acetone was added HClOA. 2, 2-dimetoxypropane (7.62 mL, 62.0 mmol) and p-toluenesulfonic acid (1.77 g, 9.30 mmol) were added to guanosine (2.00 g, 7.06 mmol) suspended in acetone (90 mL). The mixture was stirred for 24h at RT. As the reaction proceeded, the mixture became clear. The remaining precipitate was centrifuged, and the supernatants mixed and evaporated to half its original volume. Then, ammonia (25percent) was added dropwise to pH=9. The precipitate was filtered, dried and crystallized from water yielding 2’, 3’-O, O-isopropylideneguanosine (0.704 g, 2.18 mmol, 31percent).
A useful precursor for the preparation of nucleic acids
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