Boron trifluoride → HCID 18731520, compound

HRID 1884329Notes

Reaction equation

HRID 1884329 reaction equation
[C:1]([O:4][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)[CH3:2].[OH:38][C:39]1[CH:48]=[CH:47][CH:46]=[C:45]2[C:40]=1[CH2:41][CH2:42]CC2=O.B(F)(F)F>ClCCl>[C:8]([O:7][C@@H:6]1[C@H:28]([O:29][C:30](=[O:37])[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C@@H:26]([CH2:16][O:17][C:18](=[O:25])[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[O:27][C@H:5]1[O:4][C:1]1[CH:2]=[CH:42][CH:41]=[C:40]2[C:45]=1[CH2:46][CH2:47][CH2:48][C:39]2=[O:38])(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 6356Boron trifluorideHCID 81455beta-D-Ribofuranose, 1-acetate 2,3,5-tribenzoateHCID 1199215-Hydroxy-1-tetralone

Product 1

HCID 18731520HCID 18731520, compoundYield 67.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (426 mg, 0.84 mmol), 5-hydroxy-1-tetralone (122 mg, 0.75 mmol) and boron trifluoride diethyletherate (120 mg, 0.84 mmol, 106 μl) in dichloromethane (4 ml) was stirred at room temperature, under argon for 19 hours. Work-up as for Stage 1 in Example 1 then flash chromatography on silica gel (eluting with 2% acetone in toluene) gave the title compound as a colourless oil (308 mg of approx. 51% purity).

Sources & evidence

ORD record
ord-6e5d6d3b4399430a97e05ea70e8b8625
Source dataset
uspto-grants-2004_07
Patent number
US06764829B2

Reaction notes

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