Reaction #47769

Reaction equation

78

5-Amino-3-(2′,3′,5′-tri-O-acetyl-β-D-ribofuranosyl)-3H-thiazolo[4,5-d]pyrimidin-2-one

sodium phosphate

→

5-Amino-3-(2,3′-di-O-acetyl-β-D-ribofuranosyl)-3H-thiazolo[4,5-d]pyrimidin-2-one

Solvents

acetone

Conditions

Workup

1. 1
   FiltrationThe resulting clear mixture was filtered
2. 2
   Otherorganic solvent was removed under vacuum
3. 3
   ExtractionThe aqueous solution was then extracted with ethyl acetate (3×25 mL)
4. 4
   Dryingdried over MgSO4
5. 5
   Concentrationconcentrated
6. 6
   OtherThe resulting solid could be further purified in a manner similar to

Procedure

To a clear solution of 78 (500 mg) in acetone (5 mL) was added sodium phosphate buffer (pH=7.0, 0.1 M, 25 mL), upon which the solution became cloudy (white precipitate). Candida antarctica lipase resin (250 mg) was added to the mixture and the suspension was subsequently gently shaken for 10 h at room temperature. The resulting clear mixture was filtered, and organic solvent was removed under vacuum. The aqueous solution was then extracted with ethyl acetate (3×25 mL) and the organic layers were combined, dried over MgSO4, and concentrated. The resulting solid could be further purified in a manner similar to that described in Example 43, step 3.

Source