Phenyl thioxochloroformate → O-[(6aR,8R,9S,9aR)-8-(6-chloro-9H-purin-9-yl)-2,2,4,4-tetraisopropylhexahydrocyclopenta[f][1,3,5,2,4]trioxadisilocin-9-yl] O-phenyl thiocarbonate

HRID 552731Notes

Reaction equation

HRID 552731 reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@H:11]1[C@H:33]([OH:34])[C@@H:14]2[O:15][Si:16]([CH:30]([CH3:32])[CH3:31])([CH:27]([CH3:29])[CH3:28])[O:17][Si:18]([CH:24]([CH3:26])[CH3:25])([CH:21]([CH3:23])[CH3:22])[O:19][CH2:20][C@H:13]2[CH2:12]1.[CH:35]1[CH:40]=[CH:39][C:38]([O:41][C:42](Cl)=[S:43])=[CH:37][CH:36]=1>C(Cl)Cl>[C:42](=[S:43])([O:41][C:38]1[CH:39]=[CH:40][CH:35]=[CH:36][CH:37]=1)[O:34][C@@H:33]1[C@@H:14]2[O:15][Si:16]([CH:27]([CH3:29])[CH3:28])([CH:30]([CH3:32])[CH3:31])[O:17][Si:18]([CH:24]([CH3:25])[CH3:26])([CH:21]([CH3:22])[CH3:23])[O:19][CH2:20][C@H:13]2[CH2:12][C@H:11]1[N:6]1[CH:5]=[N:4][C:3]2[C:7]1=[N:8][CH:9]=[N:10][C:2]=2[Cl:1]

Participants

4

Reactant 2

HCID 70498Phenyl thioxochloroformateHCID 86607319HCID 86607319, compound

Product 1

HCID 86607321O-[(6aR,8R,9S,9aR)-8-(6-chloro-9H-purin-9-yl)-2,2,4,4-tetraisopropylhexahydrocyclopenta[f][1,3,5,2,4]trioxadisilocin-9-yl] O-phenyl thiocarbonateYield 89.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (6aR,8R,9S,9aR)-8-(6-chloro-9H-purin-9-yl)-2,2,4,4-tetraisopropylhexahydrocyclopenta[f][1,3,5,2,4]trioxadisilocin-9-ol (0.762 g, 1.44 mmol) and N,N-dimethylaminopyridine (0.529 g, 4.34 mmol) in DCM (20 mL) was added phenyl chlorothionocarbonate (0.440 mL, 3.2 mmol) and the solution was stirred for 1 h. The reaction mixture was concentrated and the residue purified by flash chromatography (0 to 50% EtOAc/hexanes) to afford the title compound (0.851 g, 88%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue purified by flash chromatography (0 to 50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-82ecfb4249074113b35f0ce336f3796e
Source dataset
uspto-grants-2011_05
Patent number
US07951810B2

Reaction notes

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