Reaction #6883

ord-b818d872f7424cc0b8956ae887e47d40

Reaction equation

Cc1cn([C@@H]2O[C@H]3[C@@H](OCc4ccccc4)[C@@H]2OC[C@H]3OCc2ccccc2)c(=O)[nH]c1=O
Nucleoside
Cc1cn([C@@H]2O[C@H]3[C@@H](OCc4ccccc4)[C@@H]2OC[C@H]3OCc2ccccc2)c(=O)[nH]c1=O
(1S,4R,5R,7R,8R)-4,8-Dibenzyloxy-7-(thymin-1-yl)-2,6-dioxabicyclo[3.2.1]octane
→
Cc1cn([C@@H]2O[C@H]3[C@@H](O)[C@@H]2OC[C@H]3O)c(=O)[nH]c1=O
nucleoside
Cc1cn([C@@H]2O[C@H]3[C@@H](O)[C@@H]2OC[C@H]3O)c(=O)[nH]c1=O
(1S,4R,5R,7R,8R)-4,8-Dihydroxy-7-(thymin-1-yl)-2,6-dioxabicyclo[3.2.1]octane

Reactants

Cc1cn([C@@H]2O[C@H]3[C@@H](OCc4ccccc4)[C@@H]2OC[C@H]3OCc2ccccc2)c(=O)[nH]c1=O
Nucleoside
Cc1cn([C@@H]2O[C@H]3[C@@H](OCc4ccccc4)[C@@H]2OC[C@H]3OCc2ccccc2)c(=O)[nH]c1=O
(1S,4R,5R,7R,8R)-4,8-Dibenzyloxy-7-(thymin-1-yl)-2,6-dioxabicyclo[3.2.1]octane

Reagents

[OH-].[OH-].[Pd+2]
palladium hydroxide on carbon

Solvents

CCO
ethanol

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherThe mixture was degassed
  2. 2
    Filtrationwas filtered off
  3. 3
    Wash(silica gel, washed with methanol, 400 cm3)
  4. 4
    Concentrationthe filtrate was concentrated to dryness under reduced pressure

Procedure

Nucleoside 18 (0.27 g, 0.60 mmol) was dissolved in absolute ethanol (20 cm3) and 20% palladium hydroxide on carbon (0.25 g) was added. The mixture was degassed and placed under an atmosphere of hydrogen. After stirring for 26 h the catalyst was filtered off (silica gel, washed with methanol, 400 cm3) and the filtrate was concentrated to dryness under reduced pressure. The residue was subjected to column chromatography on silica gel using dichloromethane/methanol (94:6, v/v) as eluent to give nucleoside 19 as white solid material (0.16 g, 98%) after evaporation of the solvents under reduced pressure.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07084125B2uspto-grants-2006_08