Réaction #67890

Équation de réaction

NaHCO3

((1S,2S,3R,4R)-2-(3-(benzyloxy)benzyl)-4-(tert-butyldimethylsilyloxy)-3-((S)-3-(tert-butyldimethylsilyloxy)octyl)cyclopentyl)methanol

triethylamine

p-toluenesulfonyl chloride

→

titled compound

Rendement 54.0%

((1S,2S,3R,4R)-2-(3-(benzyloxy)benzyl)-4-(tert-butyldimethylsilyoxy)-3-((S)-3-(tert-butyl dimethylsilyoxy)octyl)cyclopentyl)methyl 4-methylbenzenesulfonate

Rendement 54.0%

Solvants

CH2Cl2

Conditions de réaction

Traitement

1. 1
   Extractionextracted with CH2Cl2
2. 2
   Séchagedried over MgSO4
3. 3
   Autreevaporated
4. 4
   AutreThe resulting residue was purified by chromatography on a silica gel column

Mode opératoire

A solution of ((1S,2S,3R,4R)-2-(3-(benzyloxy)benzyl)-4-(tert-butyldimethylsilyloxy)-3-((S)-3-(tert-butyldimethylsilyloxy)octyl)cyclopentyl)methanol (0.3 g, 0.45 mmol) in dry CH2Cl2 (3 ml) was cooled to 0° C. under nitrogen and treated with triethylamine (0.12 ml, 0.9 mmol) and trace amount 4-(dimethylamino)pyridine (DMAP), then p-toluenesulfonyl chloride (0.13 g, 0.67 mmol) was added and the reaction was stirred at room temperature. After the reaction was completed, 20 ml saturated NaHCO3 was added and extracted with CH2Cl2, dried over MgSO4, and evaporated. The resulting residue was purified by chromatography on a silica gel column using hexane-EtOAc as eluent. to give the titled compound 0.2 g, yield 54%.

Source