Trimethyl Phosphate → 3'-Deoxy-Guanosine 5'-Monophosphate

HRID 1791096Notes

Reaction equation

[C@@H:1]1([N:9]2[C:19]3[N:18]=[C:16]([NH2:17])[NH:15][C:13](=[O:14])[C:12]=3[N:11]=[CH:10]2)[O:8][C@H:5]([CH2:6][OH:7])[CH2:4][C@H:2]1[OH:3].C[O:21][P:22](OC)([O:24]C)=[O:23].P(Cl)(Cl)(Cl)=O>>[P:22]([O:7][CH2:6][C@H:5]1[O:8][C@@H:1]([N:9]2[C:19]3[N:18]=[C:16]([NH2:17])[NH:15][C:13](=[O:14])[C:12]=3[N:11]=[CH:10]2)[C@H:2]([OH:3])[CH2:4]1)([OH:24])([OH:23])=[O:21]

Participants

Reactant 3

HCID 10541Trimethyl Phosphate

HCID 24813Phosphorus oxychloride

HCID 1354400683-Deoxyguanosine2×

Product 1

HCID 1355668253'-Deoxy-Guanosine 5'-Monophosphate

Procedure

3′-Deoxyguanosine (Compound 1, commercial product from Sigma, 50 mg, 0.19 mmol) was stirred overnight with trimethylphosphate (2 mL) and phosphorus oxychloride (53 μL, 0.57 mmol) at 6° C. The reaction was quenched by adding 20 mL of water and neutralizing with 1 M NaHCO3. DEAE-Sephadex chromatography using a linear gradient of 0–0.9 M TEAB afforded Compound 3 (yield: 45 mg, 43%).

Workup

customThe reaction was quenched
additionby adding 20 mL of water

Sources & evidence

ORD record: ord-8b1bf344afac4e4d9cf9c7827cded9e5
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07074596B2

Reaction notes

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