9-β-D-Arabinofuranosylguanine
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9-β-D-Arabinofuranosylguanine
structure -
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CAS No:
38819-10-2
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Formula:
C10H13N5O5
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Chemical Name:
9-β-D-Arabinofuranosylguanine
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Synonyms:
6H-Purin-6-one,2-amino-9-β-D-arabinofuranosyl-1,9-dihydro-;Guanine,9-β-D-arabinofuranosyl-;2-Amino-9-β-D-arabinofuranosyl-1,9-dihydro-6H-purin-6-one;2-Amino-6-hydroxy-9-(β-D-arabinofuranosyl)purine;9-β-D-Arabinofuranosylguanine;Guanine arabinoside;Araguanosine;ara-Guanosine;NSC 76352;Arabinoguanosine;A 4233;16639-98-8
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CAS No:
Description
ChEBI: A purine nucleoside in which guanine is attached to arabinofuranose via a beta-N9-glycosidic bond. It inhibits DNA synthesis and causes cell death.
Characteristics
155
-2.7
2.3±0.1 g/cm3
225°C(lit.)
775.9°C at 760 mmHg
423.1ºC
1.955
DMSO: >10mg/mL
2-8°C
Safety Information
3
22-36/37/38
26
MF8301000
Xn
P201, P202, P260, P264, P270, P281, P308+P313, P314, P405, P501
H341
9-β-D-Arabinofuranosylguanine Use and Manufacturing
To a solution of PH- 13 (50 g, 95.10mmol, 1.00equiv) in tetrahydrofuran (500 mL) with an inert atmosphere of nitrogen, was added tetrabutylammonium fluoride (95 mL, 1.00equiv, 1N in tetrahydrofuran). The resulting mixture was stirred for 12 h at 20oC. The resulting mixture was concentrated under reduced pressure. The crude was re-crystallized from methanol/ethyl acetate in the ratio of 1/5 (20 ml/g) three times. The solids were collected by filtration, and then purified by Flash with the following conditions: Column, C18 silica gel; mobile phase, waters and acetonitrile (2% acetonitrile up to 10% in 10 min); Detector, UV 254 nm. This resulted in 16 g (59%) of PH- 14 as a brown solid.1H-NMR (DMSO-d6, 400MHz): 10.44(s, 1H), 6.49(s, 2H), 6.02(s, 1H), 5.55-5.65(m, 2H), 5.10(s, 1H), 4.08(m, 2H), 3.76(m, 1H), 3.64(m, 1H).To a solution of PH- 13 (50 g, 95.l0mmol, l .OOequiv) in tetrahydrofuran (500 mL) with an inert atmosphere of nitrogen, was added tetrabutylammonium fluoride (95 mL, l .OOequiv, 1N in tetrahydrofuran). The resulting mixture was stirred for 12 h at 20C. The resulting mixture was concentrated under reduced pressure. The crude was re-crystallized from methanol/ethyl acetate in the ratio of 1/5 (20 ml/g) three times. The solids were collected by filtration, and then purified by Plash with the following conditions: Column, Cl 8 silica gel; mobile phase, waters and acetonitrile (2% acetonitrile up to 10% in 10 min); Detector, UV 254 nm. This resulted in 16 g (59%) of PH- 14 as a brown solid. 1H-NMR (DMSO-i/e, 400MHz): l0.44(s, 1H), 6.49(s, 2H), 6.02(s, 1H), 5.55- 5.65(m, 2H), 5T0(s, 1H), 4.08(m, 2H), 3.76(m, 1H), 3.64(m, 1H).
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