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 929216ノート

反応式

HRID 929216 の反応式
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

参加物

6

反応物 4

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

生成物 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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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);

後処理

  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)

出典と根拠

ORDレコード
ord-e7d50571cd584869913755b6993dd409
出典データセット
uspto-grants-2016_03
特許番号
US09290517B2

反応ノート

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