HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-Nitrophenol → .beta.-D-Ribofuranoside, 4-nitrophenyl, 2,3,5-tribenzoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 4-Nitrophenol | HCID 980 | — |
| Reactant | Boron trifluoride etherate | HCID 8000 | — |
| Reactant | beta-D-Ribofuranose, 1-acetate 2,3,5-tribenzoate | HCID 81455 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | .beta.-D-Ribofuranoside, 4-nitrophenyl, 2,3,5-tribenzoate | HCID 69914030 | 71.7% |
Reaction Steps
A solution of 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (10 g), p-nitrophenol (5.6 g, 2 eq) and boron trifluoride diethyl etherate (1.2 ml, 0.5 eq) in dry dichloromethane (100 ml) was allowed to stand at room temperature overnight. Thin-layer chromatography on silica gel [Eluant EtOAc:CHCl3:Hexanes 1:2:4] then indicated essentially complete conversion to a slightly less polar material. The solution was washed with aq bicarbonate and processed conventionally. Flash chromatography on silica gel [eluant EtOAc:CHCl3:Hexanes 1:2:8] then afforded 8.29 g of title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06764829B2 |
| Source dataset | uspto-grants-2004_07 |
| ORD ID | ord-9a4e42910eb7401b9d20cf3efc4841df |
| Source note | uspto-grants-2004_07 |