2,6-Dichloropurine riboside
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2,6-Dichloropurine riboside
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CAS No:
13276-52-3
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Formula:
C10H10Cl2N4O4
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Chemical Name:
2,6-Dichloropurine riboside
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Synonyms:
2, 6-DICHLOROPURINE RIBOSIDE (2,6DClPR);2,6-Dichloropurine r;2,6-Dichloro-9-β-D-ribofuranosyl-9H-purine;2,6-dichloropuine nuceotide;(2R,3R,4S,5R)-2-(2,6-Dichloro-9H-purin-9-yl)-5-(hydroxyMethyl)tetrahydrofuran-3,4-diol;2,6-dichloro-9-(β-D-ribofuranosyl)purine;2,6-Dichloro-9-(beta-D-ribofuranosyl)purine;2,6-Dichloropurine riboside###13276-52-3
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CAS No:
Characteristics
114
1.2
2.14±0.1 g/cm3(Predicted)
>190°C (dec)
542.2±60.0 °C(Predicted)
310.2±32.9 °C
1.854
Refrigerator
2,6-Dichloropurine riboside Use and Manufacturing
Under a nitrogen atmosphere, to a three-necked flask equipped with a dropping funnel, 450 ml of all-acetyl protected 2, 6-dichloropurine (0.1 mole) and anhydrous methanol were added, Stir until the system is completely clear, cooled to 0-10 , acetyl chloride (1.2mol) was slowly added dropwise, the addition was complete, the reaction was continued for 1.5 hours, TLC detection reaction was complete;To the reaction system, solid potassium carbonate was added in portions until pH = 7-8, filtered, the filtrate was concentrated to dryness, water was added, Extracted three times with 250 ml of ethyl acetate, the combined extracts were dried over anhydrous sodium sulfate, filtered and the filtrate was concentrated to dryness.Recrystallization by adding 140 ml of isopropanol gave 27.3 g of 2, 6-dichloropurine as a white solid in 85percent yield, 2-nitro-6-chlorotriacetylpurine nucleoside (4, 4.6g, 10mmol) was added to a saturated solution of saturated hydrogen chloride gas in ethanol (20 mL), and stirred at room temperature for 10 hours, the solvent was removed under reduced pressure, to give viscous material was recrystallized from ethanol, to obtain the 2, 6-dichloropurine nucleoside in a yield of 82percent.Under a nitrogen atmosphere, a full benzoyl-protected 2, 6-dichloropurine (0.1 mole) and anhydrous methanol (550 ml) were placed in a three-necked flask equipped with a dropping funnel, Stir until the system is completely clear, cooled to 0-10 ° C, acetyl chloride (1.5 moles) was slowly added dropwise, the addition was complete, the reaction was continued for 4 hours, the reaction was complete by TLC;The solid sodium carbonate was added portionwise to the reaction system until PH = 7-8, filtered, the filtrate was concentrated to dryness, water was added, The mixture was extracted three times with 350 ml of ethyl acetate. The combined extracts were dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated to dryness and recrystallized from 160 ml of isopropanol to give 26.3 g of 2, 6-dichloro purine nucleoside as a white solid Rate of 82percent
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