Reaktion #715933

Reaktionsgleichung

toluene

(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-one

N-methylmorpholine

TMSCI

→

product

Ausbeute 100.0%

(3R,4S,5R,6R)-3,4,5-tri((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one

Ausbeute 100.0%

Lösungsmittel

water

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   workup.ADDITIONAfter the completion of dropwise addition
3. 3
   workup.STIRRINGThen the mixture was stirred overnight while the temperature
4. 4
   Temperaturwas maintained at 25° C
5. 5
   Sonstigethe completion of reaction
6. 6
   SonstigeThe organic phase was collected
7. 7
   Waschenwashed with sodium dihydrogen phosphate for one time, with water for one time
8. 8
   Trocknenwith a saturated sodium chloride solution for one time, dried
9. 9
   Einengenconcentrated

Vorschrift

(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-one (85 g, 0.47 mol) was suspended in THF (tetrahydrofuran) (932 mL). To the resulting mixture was added N-methylmorpholine (405 mL, 4.78 mol). Then the resulting mixture was cooled to −5° C. under a nitrogen protection, and TMSCI (trimethylsilane chloride) (360 mL, 4.78 mol) was added dropwise thereto. After the completion of dropwise addition, the resulting mixture was stirred at room temperature for 1 h and at 35° C. for 5 hr. Then the mixture was stirred overnight while the temperature was maintained at 25° C. TLC indicated the completion of reaction. To the reaction mixture was added toluene (200 mL) and added dropwise water (1 L) in an ice-water bath. The organic phase was collected, washed with sodium dihydrogen phosphate for one time, with water for one time, and with a saturated sodium chloride solution for one time, dried and concentrated to produce 218 g of a product in a yield of 100%.

Quelle