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ChemicalBook CAS DataBase List Adenosine, 5'-sulfaMate
25030-31-3

Adenosine, 5'-sulfaMate synthesis

7synthesis methods
-

Yield:25030-31-3 89%

Reaction Conditions:

with tetrabutyl ammonium fluoride in tetrahydrofuran at 20; for 0.5 h;

Steps:



TBAF (1.0 M in THF, 250 μL, 0.25 mmol, 2.5 equiv) was added dropwise to a solution of bis(TBS)sulfamoyladenosine 3 (57.4 mg, 0.1 mmol) in anhyd THF (4.0 mL). The reaction mixture was stirred at rt for 30 min. The solvent was then evaporated. The residue was purified by column chromatography (elution with 5:1 EtOAc/MeOH) to afford 6 as a white solid (31 mg, 89%).[00172] TLC: i/0.18 (6:1 EtOAc/MeOH). 1H-NMR (500 MHz, DMSOd6): δ 8.30 (s, IH), 8.15 (s, IH), 7.60 (br s, 2H), 7.31 (br s, 2H), 5.93 (d, IH, J= 5.3), 5.62 (d, IH, J= 6.0), 5.44 (d, IH, J= 5.4), 4.63 (app q, IH, J= 5.4), 4.29 (dd, IH, J= EPO 10.7, 3.8), 4.23 (app q, IH, J= 4.9), 4.19 (dd, IH, J= 10.6, J= 6.0), 4.14 (m, IH). 13C-NMR (125 MHz5 DMSOd6): δ 156.1, 152.7, 149.4, 139.4, 119.1, 87.5, 81.5, 73.0, 70.3, 68.7. ESI-MS m/z: (pos) 347.1 [M+H]+, 368.9 [M+Na]+; (neg) 344.9 [M- H]", 380.9 [M+Cl]-.

References:

WO2006/113615,2006,A2 Location in patent:Page/Page column 90-91; 7/23

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