4-Nitrophenol → .beta.-D-Ribofuranoside, 4-nitrophenyl, 2,3,5-tribenzoate

HRID 1884326Notes

Reaction equation

HRID 1884326 reaction equation
C(O[C@@H:5]1[O:27][C@H:26]([CH2:28][O:29][C:30](=[O:37])[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C@@H:16]([O:17][C:18](=[O:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C@H:6]1[O:7][C:8](=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=O)C.[CH:38]1[C:43]([N+:44]([O-:46])=[O:45])=[CH:42][CH:41]=[C:40]([OH:47])[CH:39]=1.B(F)(F)F.CCOCC>ClCCl>[C:8]([O:7][C@@H:6]1[C@H:16]([O:17][C:18](=[O:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C@@H:26]([CH2:28][O:29][C:30](=[O:37])[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[O:27][C@H:5]1[O:47][C:40]1[CH:41]=[CH:42][C:43]([N+:44]([O-:46])=[O:45])=[CH:38][CH:39]=1)(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 8000Boron trifluoride etherateHCID 81455beta-D-Ribofuranose, 1-acetate 2,3,5-tribenzoate

Product 1

HCID 69914030.beta.-D-Ribofuranoside, 4-nitrophenyl, 2,3,5-tribenzoateYield 71.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  1. washThe solution was washed with aq bicarbonate

Sources & evidence

ORD record
ord-9a4e42910eb7401b9d20cf3efc4841df
Source dataset
uspto-grants-2004_07
Patent number
US06764829B2

Reaction notes

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