Boron trifluoride etherate → 9-(2,5-di-O-acetyl-3-bromo-3-deoxy-beta-D-xylofuranosyl)adenine

HRID 1979055Notes

Reaction equation

C(O[C@@H:5]1[C@@H:9]([CH2:10][O:11][C:12](=[O:14])[CH3:13])[O:8][C@@H:7]([N:15]2[C:24]3[N:23]=[CH:22][N:21]=[C:19]([NH2:20])[C:18]=3[N:17]=[CH:16]2)[C@@H:6]1[OH:25])(=O)C.B(F)(F)F.[CH3:30][CH2:31][O:32]CC.P(Br)(Br)[Br:36]>>[C:31]([O:25][C@@H:6]1[C@@H:5]([Br:36])[C@@H:9]([CH2:10][O:11][C:12](=[O:14])[CH3:13])[O:8][C@H:7]1[N:15]1[CH:16]=[N:17][C:18]2[C:24]1=[N:23][CH:22]=[N:21][C:19]=2[NH2:20])(=[O:32])[CH3:30]

Participants

Reactant 3

HCID 8000Boron trifluoride etherate

HCID 24614Phosphorus tribromide

HCID 186519173',5'-Di-o-acetyladenosine

Product 1

HCID 109825609-(2,5-di-O-acetyl-3-bromo-3-deoxy-beta-D-xylofuranosyl)adenine

Procedure

This compound is prepared by a in situ acyloxonium ion generated by treating 3′,5′-di-O-acetyladenosine with boron trifluoride etherate followed by phosphorus tribromide according to the procedure of Kondo, K., Adachi, T., and Inoue, I. (1977), J. Org. Chem., 42:3967. The title compound can also be formed by treating adenosine with tetraacetoxysilane and phosphorus tribromide in the presence of boron trifluoride etherate.

Sources & evidence

ORD record: ord-a69209c751ed4425b041218a9d3ee512
Source dataset: uspto-grants-2001_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06239265B1

Reaction notes

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