Reaktion #74485

Reaktionsgleichung

3-(chloro(2-chloro-5-((3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)phenyl)methyl)-6-ethoxypyridazine

AIBN

tributyltin hydride

→

3-(2-Chloro-5-((3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)benzyl)-6-ethoxypyridazine

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas coded to room temperature
2. 2
   Sonstigetoluene was removed on evaporator
3. 3
   SonstigeThe crude α/β mixture was purified by silica gel column chromatography with KF pad (eluent: hexane/EtOAc mixture (60/40; v/v))
4. 4
   SonstigeThe purified α/β mixture was separated
5. 5
   Sonstigeobtained α configured product (123 mg; 0.16 mmol) and β configured product (105 mg; 0.14 mmol) as colorless oil

Vorschrift

To a solution of 3-(chloro(2-chloro-5-((3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)phenyl)methyl)-6-ethoxypyridazine (589 mg; 0.73 mmol) in anhydrous toluene (10 mL) was added catalytic amounts of AIBN and tributyltin hydride (0.3 mL; 1.10 mmol) at room temperature under nitrogen gas. The reaction solution was then heated at 80° C. until reaction was completed. The solution was coded to room temperature and toluene was removed on evaporator. The crude α/β mixture was purified by silica gel column chromatography with KF pad (eluent: hexane/EtOAc mixture (60/40; v/v)). The purified α/β mixture was separated by using Gilson prep HPLC system and then obtained α configured product (123 mg; 0.16 mmol) and β configured product (105 mg; 0.14 mmol) as colorless oil.

Quelle