Réaction #609359

Équation de réaction

Hg(OAc)2

(2R,3R,4R,5R)-1,3,4,5-tetrakis(benzyloxy)hept-6-en-2-ol

potassium chloride

→

(((2S,3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)methyl)mercury(II) chloride

Rendement 72.0%

Solvants

EtOAc

THF

THF

Conditions de réaction

Traitement

1. 1
   workup.WAITAfter 30 minutes
2. 2
   Lavagewashed with water (20 mL)
3. 3
   Séchagedried over anhydrous sodium sulfate
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated in vacuo
6. 6
   AutreThe material thus obtained
7. 7
   Autrewas purified by silica gel chromatography
8. 8
   Lavageeluting with 30% EtOAc in petroleum ether

Mode opératoire

To a suspension of Hg(OAc)2 (0.88 g, 2.8 mmol, 1.0 equiv) in dry THF (50 mL) under nitrogen atmosphere was added (2R,3R,4R,5R)-1,3,4,5-tetrakis(benzyloxy)hept-6-en-2-ol (1.5 g, 2.78 mmol, 1.0 equiv) dissolved in 20 mL of dry THF. The reaction was stirred at room temperature for 16 hours and then a saturated aqueous solution of potassium chloride (0.50 g, 4.5 mmol, 1.6 equiv) was added. After 30 minutes, the reaction mixture was diluted with EtOAc (80 mL), washed with water (20 mL), dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The material thus obtained was purified by silica gel chromatography, eluting with 30% EtOAc in petroleum ether, to give (((2S,3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)methyl)mercury(II) chloride as a pale yellow oil (1.5 g, 72%). 1H NMR (300 MHz, CDCl3) δ 7.45-7.15 (m, 20H), 4.62-4.39 (m, 7H), 4.33 (d, J=11.9 Hz, 1H), 4.24-4.11 (m, 1H), 4.08 (ddd, J=7.7, 5.9, 2.2 Hz, 1H), 3.89-3.76 (m, 2H), 3.72 (dd, J=4.2, 2.3 Hz, 1H), 3.68-3.57 (m, 1H), 3.39 (dd, J=8.5, 2.9 Hz, 1H), 2.18-1.96 (m, 2H). ESI (M+H2O) 792.0; calc for C35H37ClHgO5 774.2.

Source