Methanol → p-Tolyl methyl sulfone

HRID 1355341Notes

Reaction equation

[C:1](NC1NC(=O)C2N=CN(C=2N=1)[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1OC)(=O)C(C)C.[C:27]1([CH3:37])[CH:32]=[CH:31][C:30]([S:33](Cl)(=[O:35])=[O:34])=[CH:29][CH:28]=1.CO>N1C=CC=CC=1>[S:33]([CH3:1])([C:30]1[CH:31]=[CH:32][C:27]([CH3:37])=[CH:28][CH:29]=1)(=[O:35])=[O:34]

Participants

Conditions

Temperature: 0 °C

Procedure

(see FIG. 8B) N2-Isobutyryl-2′-O-methylguanosine (6) (Inoue et al., Nucleic Acids Res. 1987, 15, 6131-6148, and is incorporated by reference herin in its entirety) (1.6 g, 4.36 mmol) was dissolved in dry pyridine (25 mL) and the solution was cooled to 0° C. while protected from moisture. p-Toluenesulfonyl chloride (1.0 g, 5.23 mmol) was added and the reaction mixture was left at 0-3° C. for 48 h. MeOH (10 mL) was added and the mixture evaporated to a syrup. After standard work up and column chromatography using 1-2% MeOH in CH2Cl2, 7 was obtained as a colorless foam, 1.06 g (47%), 1H NMR δ12.25 (br s, 1H, NH), 9.55 (br s, 1H, NH), 7.83 (d, JH,H=8.3, 2H, Ts), 7.78 (s, 1H, H8), 7.42 (d, JH,H=8.3, 2H, Ts), 5.83 (d, J1′,2′=6.2, 1H, H1′), 4.82 (app t, J2′,3′=5.7, 1H, H2′), 4.64 (m, 1H, H3′), 4.37 (dd, J5′,4′=2.2, J5′,5″=10.3, 1H, H5′), 5.23 (dd, J4′,5″=2.9, J4′,3′=5.2, 1H, H4′), 4.29 (dd, J5″,4′=2.9, J5″,5′=10.3, 1H, H5″), 3.47 (s, 3H), OMe), 2.76 (m, 1H, CH(CH3)2), 2.51 (s, 3H, Ts-Me),1.29 (m, 6H, 2×Me).

Workup

customthe mixture evaporated to a syrup

Sources & evidence

ORD record: ord-f7224d36267c4caba0ec685734966891
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06586238B1

Reaction notes

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