Reaktion #684658

Reaktionsgleichung

water chloroform

9-(2,3,5-Tri-O-acetyl-β-D-ribofuranosyl)-6-hydroxymethyl-1,6-dihydropurine

9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-6-hydroxymethyl-1,6-dihydropurine

sodium hydride

mesyl chloride

→

II

Ausbeute 91.0%

9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-6-mesyloxymethyl-1,6-dihydropurine

Ausbeute 91.0%

Lösungsmittel

dimethoxyethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled to -10° to -15° C
2. 2
   Sonstigethe chloroform layer thus separated
3. 3
   Waschenwas washed with 0.5% aqueous sodium hydrogen carbonate
4. 4
   Trocknenwith water, dried over anhydrous sodium sulfate
5. 5
   Einengenconcentrated

Vorschrift

9-(2,3,5-Tri-O-acetyl-β-D-ribofuranosyl)-6-hydroxymethyl-1,6-dihydropurine (VI) (217 mg.) obtained in (2) was dissolved in purified anhydrous dimethoxyethane (10 ml.) and cooled to -10° to -15° C. To the cooled solution were added sodium hydride (76 mg., 3 moles) and mesyl chloride (180 mg., 3 moles), successively. The reaction was conducted at 0° - 5° C. for 17 hours. The reaction mixture was then treated with water-chloroform and the chloroform layer thus separated was washed with 0.5% aqueous sodium hydrogen carbonate, then with water, dried over anhydrous sodium sulfate and concentrated to yield II as a pale-yellow oil (235 mg., yield: 91%). This substance is unstable and decomposes in chloroform within 2-3 hours.

Quelle