Triphenylphosphine → (3R,3aR,6R,6aS)-6-((5-([1,1'-biphenyl]-4-yl)-6-chloro-1H-imidazo[4,5-b]pyridin-2-yl)thio)hexahydrofuro[3,2-b]furan-3-ol

HRID 929216Notes

Reaction equation

HRID 929216 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.[C:32]1([C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)[CH:37]=[CH:36][C:35]([C:38]2[N:43]=[C:42]3[N:44]=[C:45]([SH:55])[N:46](COCC[Si](C)(C)C)[C:41]3=[CH:40][C:39]=2[Cl:56])=[CH:34][CH:33]=1.[Si](O[C@H:71]1[C@H:75]2[O:76][CH2:77][C@H:78]([OH:79])[C@H:74]2[O:73][CH2:72]1)(C(C)(C)C)(C)C>C1COCC1>[C:32]1([C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)[CH:37]=[CH:36][C:35]([C:38]2[N:43]=[C:42]3[N:44]=[C:45]([S:55][C@H:71]4[C@H:75]5[O:76][CH2:77][C@@H:78]([OH:79])[C@H:74]5[O:73][CH2:72]4)[NH:46][C:41]3=[CH:40][C:39]=2[Cl:56])=[CH:34][CH:33]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 11196262D-Glucitol, 1,4:3,6-dianhydro-5-O-[(1,1-dimethylethyl)dimethylsilyl]-HCID 178504257HCID 178504257, compound

Product 1

HCID 90067164(3R,3aR,6R,6aS)-6-((5-([1,1'-biphenyl]-4-yl)-6-chloro-1H-imidazo[4,5-b]pyridin-2-yl)thio)hexahydrofuro[3,2-b]furan-3-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triphenylphosphine (34.1 mg, 0.130 mmol) and DEAD (0.021 ml, 0.130 mmol) were added to a stirred mixture of 5-([1,1′-biphenyl]-4-yl)-6-chloro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazo[4,5-b]pyridine-2-thiol (30.4 mg, 0.065 mmol) and (3S,3aR,6R,6aS)-6-((tert-butyldimethylsilyl)oxy)hexahydrofuro[3,2-b]furan-3-ol (25.4 mg, 0.097 mmol) in THF (1 ml) and the mixture was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure and the resulting residue was purified by preparative TLC, eluting with EtOAc/isohexane (2:8) to give the title compound. LC-MS: calculated for C36H48ClN3O4SSi2 709.26 observed m/e: 710.42 (M+H)+ (Rt 1.59/2 min);

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe resulting residue was purified by preparative TLC
  3. washeluting with EtOAc/isohexane (2:8)

Sources & evidence

ORD record
ord-e7d50571cd584869913755b6993dd409
Source dataset
uspto-grants-2016_03
Patent number
US09290517B2

Reaction notes

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