Tetrafluoroboric acid → 9-(2,3,5-Tri-O-benzyl-beta-D-arabinofuranosyl)-2-fluoroadenine

HRID 1195207Notes

Reaction equation

HRID 1195207 reaction equation
N[C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[O:31][C@H:30]([CH2:32][O:33][CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C@@H:21]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C@@H:12]2[O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:4]([NH2:41])[N:3]=1.[F:42][B-](F)(F)F.[H+]>>[CH2:14]([O:13][C@H:12]1[C@H:21]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C@@H:30]([CH2:32][O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[O:31][C@H:11]1[N:8]1[CH:7]=[N:6][C:5]2[C:9]1=[N:10][C:2]([F:42])=[N:3][C:4]=2[NH2:41])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

3

Reactant 2

HCID 28118Tetrafluoroboric acidHCID 108969412-Amino-9-(2,3,5-tri-O-benzyl-beta-D-arabinofuranosyl)adenine

Product 1

HCID 109627089-(2,3,5-Tri-O-benzyl-beta-D-arabinofuranosyl)-2-fluoroadenine

Procedure

The process of claim 1 wherein in addition the 2-amino group of (V) is replaced with a 2-fluoro group by reaction with fluoroboric acid in an organic solvent for the reaction to form 9-(2,3,5 tri-O-benzyl-beta-D-arabinofuranosyl)-2-fluoroadenine (VI) and wherein (VI) is treated in a reaction mixture with hydrogen and palladium chloride in an organic solvent and in a sealed vessel under pressure to produce 9-beta-D-arabinofuranosyl-2-fluoroadenine (VII) which is separated from the reaction mixture.

Sources & evidence

ORD record
ord-e18dd497483d4055bc1e72ea298baae1
Source dataset
uspto-grants-1992_05
Patent number
US05110919

Reaction notes

Loading…