(1S,4R,5R,7R,8R)-4,8-Dibenzyloxy-7-(thymin-1-yl)-2,6-Dioxabicyclo [3.2.1]Octane → (1S,4R,5R,7R,8R)-4,8-Dihydroxy-7-(thymin-1-yl)-2,6-dioxabicyclo[3.2.1]octane

HRID 6787

Reaction equation

HRID 6787 reaction equation
C([O:8][C@H:9]1[C@@H:15]2[C@@H:16]([O:17]CC3C=CC=CC=3)[C@@H:12]([C@H:13]([N:25]3[CH:33]=[C:31]([CH3:32])[C:29](=[O:30])[NH:28][C:26]3=[O:27])[O:14]2)[O:11][CH2:10]1)C1C=CC=CC=1>C(O)C.[OH-].[OH-].[Pd+2]>[OH:8][C@H:9]1[C@@H:15]2[C@@H:16]([OH:17])[C@@H:12]([C@H:13]([N:25]3[CH:33]=[C:31]([CH3:32])[C:29](=[O:30])[NH:28][C:26]3=[O:27])[O:14]2)[O:11][CH2:10]1

Participants

4

Reactant 1

HCID 57198644(1S,4R,5R,7R,8R)-4,8-Dibenzyloxy-7-(thymin-1-yl)-2,6-Dioxabicyclo [3.2.1]Octane

Product 1

HCID 67527748(1S,4R,5R,7R,8R)-4,8-Dihydroxy-7-(thymin-1-yl)-2,6-dioxabicyclo[3.2.1]octane

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

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.

Workup

  1. customThe mixture was degassed
  2. filtrationwas filtered off
  3. wash(silica gel, washed with methanol, 400 cm3)
  4. concentrationthe filtrate was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-b818d872f7424cc0b8956ae887e47d40
Source dataset
uspto-grants-2006_08
Patent number
US07084125B2

Linked notes

Loading…