[(3aR,4R,6R,6aR)-2,2-dimethyl-6-(6-{[2-(trifluoromethyl)phenyl]ethynyl}-9H-purin-9-yl)tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]methyl sulfamate → [(2R,3S,4R,5R)-3,4-dihydroxy-5-(6-{[2-(trifluoromethyl)phenyl]ethynyl}-9H-purin-9-yl)tetrahydrofuran-2-yl]methyl sulfamate

HRID 552747Notes

Reaction equation

HRID 552747 reaction equation
[S:1](=[O:37])(=[O:36])([O:3][CH2:4][C@@H:5]1[C@@H:12]2[C@@H:8]([O:9]C(C)(C)[O:11]2)[C@H:7]([N:15]2[CH:23]=[N:22][C:21]3[C:16]2=[N:17][CH:18]=[N:19][C:20]=3[C:24]#[C:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[C:32]([F:35])([F:34])[F:33])[O:6]1)[NH2:2]>C(O)(C(F)(F)F)=O.O>[S:1](=[O:36])(=[O:37])([O:3][CH2:4][C@@H:5]1[C@@H:12]([OH:11])[C@@H:8]([OH:9])[C@H:7]([N:15]2[CH:23]=[N:22][C:21]3[C:16]2=[N:17][CH:18]=[N:19][C:20]=3[C:24]#[C:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[C:32]([F:35])([F:34])[F:33])[O:6]1)[NH2:2]

Participants

3

Reactant 1

HCID 86607327[(3aR,4R,6R,6aR)-2,2-dimethyl-6-(6-{[2-(trifluoromethyl)phenyl]ethynyl}-9H-purin-9-yl)tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]methyl sulfamate

Product 1

HCID 58296166[(2R,3S,4R,5R)-3,4-dihydroxy-5-(6-{[2-(trifluoromethyl)phenyl]ethynyl}-9H-purin-9-yl)tetrahydrofuran-2-yl]methyl sulfamateYield 52%

Reagents, catalysts & solvents 1

HCID 22392675Trifluoroacetic acid waterSolvent

Procedure

[(3aR,4R,6R,6aR)-2,2-dimethyl-6-(6-{[2-(trifluoromethyl)phenyl]ethynyl}-9H-purin-9-yl)tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]methyl sulfamate (0.185 g, 0.343 mmol) was stirred in 3 mL of 90% TFA/H2O for 4 h at r.t. The solvent was removed and the crude product was purified by flash chromatography (1 to 10% MeOH/CH2Cl2) to isolate the title compound (0.0882 g, 52%).

Workup

  1. customThe solvent was removed
  2. customthe crude product was purified by flash chromatography (1 to 10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-7c657d4b47ff4f1b997776ea35c676ec
Source dataset
uspto-grants-2011_05
Patent number
US07951810B2

Reaction notes

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