Sodium Hydroxide → (1R,3R,4S,7R)-1-(Hydroxymethyl)-7-benzyloxy-3-(thymin-1-yl)-2,5-dioxabicyclo-[2.2.1]heptane

HRID 1827448Notes

Reaction equation

[CH2:1]([O:8][C@H:9]1[C:13]([CH2:20][O:21]S(C)(=O)=O)([CH2:14][O:15]S(C)(=O)=O)[O:12][C@@H:11]([N:26]2[CH:34]=[C:32]([CH3:33])[C:30](=[O:31])[NH:29][C:27]2=[O:28])[C@@H:10]1OS(C)(=O)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C.O>[OH:21][CH2:20][C@:13]12[C@H:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[C@H:10]([O:15][CH2:14]1)[C@H:11]([N:26]1[CH:34]=[C:32]([CH3:33])[C:30](=[O:31])[NH:29][C:27]1=[O:28])[O:12]2

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of nucleoside 11 (329 mg, 0.54 mmol) in ethanol/water (10 cm3, 1:1, v/v) was added 6M NaOH (aq) (0.9 ml, 5.4 mmol). The mixture was refluxed at 80° C. for 43 h followed by evaporation to dryness under reduced pressure. The residue was purified by silica gel column chromatography using dichloromethane/methanol (2.4% methanol, v/v) as eluent to afford nucleoside 12 (85 mg, 44%). δC ((CD3)2SO) 163.8, 150.3, 138.0, 135.8, 128.3, 127.7, 127.5, 108.0, 90.2, 86.5, 86.4, 79.3, 76.5, 72.5, 71.2, 57.2, 40.2, 40.0, 39.8. 39.6, 39.4, 39.2, 39.0, 12.3.

Workup

customfollowed by evaporation to dryness under reduced pressure
customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-42f47463bd344747a14ec9506c5f6f1e
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07053207B2

Reaction notes

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