Reaction #56623

ord-1deef8db739946a69e53f436f0756d25

Reaction equation

CC(=O)OC[C@H]1O[C@@H](n2c(Cl)cc3cc(Cl)c(Cl)cc32)[C@H](O)[C@@H]1O
2,5,6-Trichloro-1-(5-O-acetyl-β-D-ribofuranosyl)indole
CCC(=O)Cl
propionyl chloride
→
CCC(=O)c1c(Cl)n([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c2cc(Cl)c(Cl)cc12
2,5,6-trichloro-3-propionyl-1-(β-D-ribofuranosyl)indole

Reactants

—
3-propionyl
CC(=O)OC[C@H]1O[C@@H](n2c(Cl)cc3cc(Cl)c(Cl)cc32)[C@H](O)[C@@H]1O
2,5,6-Trichloro-1-(5-O-acetyl-β-D-ribofuranosyl)indole
CCC(=O)Cl
propionyl chloride

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Procedure

The same procedure was used for the synthesis of the 3-propionyl derivative 4.47 (FIG. 6A). 2,5,6-Trichloro-1-(5-O-acetyl-β-D-ribofuranosyl)indole (4.39, FIG. 6A) was acylated under Friedel-Crafts conditions with propionyl chloride and deprotected in two steps to yield the desired 2,5,6-trichloro-3-propionyl-1-(β-D-ribofuranosyl)indole (4.47, FIG. 6A).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07419963B2uspto-grants-2008_09