Acetonitrile → 5'-O-acetyl-2',3'-dideoxyadenosine

HRID 1030775

반응식

HRID 1030775 반응식
C(#N)C.[C:4]([O:7][C@@H:8]1[C@@H:12](Br)[C@@H:11]([CH2:14][O:15][C:16](=[O:18])[CH3:17])[O:10][C@H:9]1[N:19]1[CH:27]=[N:26][C:25]2[C:20]1=[N:21][CH:22]=[N:23][C:24]=2[NH2:28])(=[O:6])[CH3:5].[Br-].[Br-].C([N+]1C=CC(C2C=C[N+](CCCCCCC)=CC=2)=CC=1)CCCCCC.[H][H]>[C].[Pd].C(N(CC)CC)C>[C:16]([O:15][CH2:14][C@H:11]1[O:10][C@@H:9]([N:19]2[C:20]3[N:21]=[CH:22][N:23]=[C:24]([NH2:28])[C:25]=3[N:26]=[CH:27]2)[CH:8]=[CH:12]1)(=[O:18])[CH3:17].[C:16]([O:15][CH2:14][C@H:11]1[O:10][C@@H:9]([N:19]2[C:20]3[N:21]=[CH:22][N:23]=[C:24]([NH2:28])[C:25]=3[N:26]=[CH:27]2)[CH2:8][CH2:12]1)(=[O:18])[CH3:17].[C:4]([O:7][C@@H:8]1[CH2:12][C@@H:11]([CH2:14][O:15][C:16](=[O:18])[CH3:17])[O:10][C@H:9]1[N:19]1[C:20]2[N:21]=[CH:22][N:23]=[C:24]([NH2:28])[C:25]=2[N:26]=[CH:27]1)(=[O:6])[CH3:5]

참가 물질

9

반응물 4

HCID 6342AcetonitrileHCID 802621,1'-Diheptyl-4,4'-bipyridinium dibromideHCID 109825609-(2,5-di-O-acetyl-3-bromo-3-deoxy-beta-D-xylofuranosyl)adenineHCID 178418361HCID 178418361, 화합물

생성물 3

HCID 11022122((2S,5R)-5-(6-Amino-9H-purin-9-yl)-2,5-dihydrofuran-2-yl)methyl acetateHCID 149894675'-O-acetyl-2',3'-dideoxyadenosine수율 11%HCID 149894682',5'-di-O-acetyl-3'-deoxyadenosine수율 3%

시약·촉매·용매 2

HCID 178418390HCID 178418390, 화합물촉매HCID 8471Triethylamine용매

실험 절차

To 120 ml of acetonitrile were added 1.50 g (3.62 mmols) of 9-(2,5-di-O-acetyl-3-bromo-3-deoxy-β-D-xylofuranosyl) adenine, 946 mg (1.84 mmol) of N,N'-diheptyl-4,4'-bipyridinium dibromide, 1.13 g of 10% palladium-carbon (water content, 50%) and 2.5 ml of triethylamine. The mixture was stirred for 2 hours at room temperature in a hydrogen atmosphere. The analysis by HPLC reveals that the raw material disappeared and 5'-O-acetyl-2',3'-didehydro-2',3'-dideoxyadenosine (85), 5'-O-acetyl-2',3'-dideoxyadenosine (11%) and 2',5'-di-O-acetyl-3'-deoxyadenosine (3%) were formed.

출처 및 근거

ORD 기록
ord-ae99ac58e91b4559a1428c60995f923b
출처 데이터셋
uspto-grants-1992_04
특허 번호
US05106962

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