HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetonitrile → 5'-O-acetyl-2',3'-dideoxyadenosine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetonitrile | HCID 6342 | — |
| Reactant | 1,1'-Diheptyl-4,4'-bipyridinium dibromide | HCID 80262 | — |
| Reactant | 9-(2,5-di-O-acetyl-3-bromo-3-deoxy-beta-D-xylofuranosyl)adenine | HCID 10982560 | — |
| Reactant | HCID 178418361 | HCID 178418361 | — |
| Catalyst | HCID 178418390 | HCID 178418390 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | ((2S,5R)-5-(6-Amino-9H-purin-9-yl)-2,5-dihydrofuran-2-yl)methyl acetate | HCID 11022122 | — |
| Product | 5'-O-acetyl-2',3'-dideoxyadenosine | HCID 14989467 | 11% |
| Product | 2',5'-di-O-acetyl-3'-deoxyadenosine | HCID 14989468 | 3% |
Reaction Steps
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.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05106962 |
| Source dataset | uspto-grants-1992_04 |
| ORD ID | ord-ae99ac58e91b4559a1428c60995f923b |
| Source note | uspto-grants-1992_04 |