(6-(2-Amino-6-oxo-1,6-dihydropurin-9-yl)-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl hydrogen sulfate → ((2R,3R,4S,5R)-5-(2-amino-6-oxo-1,6-dihydropurin-9-yl)-3,4-dihydroxytetrahydro-furan-2-yl)methyl hydrogen sulfate

HRID 1921908Notes

Reaction equation

HRID 1921908 reaction equation
[S:1]([OH:27])([O:4][CH2:5][CH:6]1[CH:13]2[CH:9]([O:10]C(C)(C)[O:12]2)[CH:8]([N:16]2[CH:24]=[N:23][C:22]3[C:21](=[O:25])[NH:20][C:19]([NH2:26])=[N:18][C:17]2=3)[O:7]1)(=[O:3])=[O:2]>O>[S:1]([OH:27])([O:4][CH2:5][C@@H:6]1[C@H:13]([OH:12])[C@H:9]([OH:10])[C@H:8]([N:16]2[CH:24]=[N:23][C:22]3[C:21](=[O:25])[NH:20][C:19]([NH2:26])=[N:18][C:17]2=3)[O:7]1)(=[O:2])=[O:3]

Participants

3

Reactant 1

HCID 136064682(6-(2-Amino-6-oxo-1,6-dihydropurin-9-yl)-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl hydrogen sulfate

Product 1

HCID 136395876((2R,3R,4S,5R)-5-(2-amino-6-oxo-1,6-dihydropurin-9-yl)-3,4-dihydroxytetrahydro-furan-2-yl)methyl hydrogen sulfate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of crude 12 (8.11 mmol) in water (8 mL) was added Amberlite 120 acidic resin (0.300 g). The mixture was heated to 70° C. for 4 hours, and then filtered while hot through a sintered glass frit. The water was removed under reduced pressure and ambient temperature to yield 5 (0.244 g, 83% for two steps).

Workup

  1. filtrationfiltered while hot through a sintered glass frit
  2. customThe water was removed under reduced pressure and ambient temperature
  3. customto yield 5 (0.244 g, 83% for two steps)

Sources & evidence

ORD record
ord-cece247ce1b44cffa8e8c0fa8c6b35eb
Source dataset
uspto-grants-2012_05
Patent number
US08173797B2

Reaction notes

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