Reaction #6880

Reaction equation

hydrochloric acid

nucleoside

1-(2-O-acetyl-6-O-benzoyl-3,5-di-O-benzyl-β-D-allofuranosyl)thymine

sodium methoxide

→

nucleoside

1-(3,5-di-O-benzyl-β-D-allofuranosyl)thymine

Solvents

methanol

Conditions

Workup

1. 1
   workup.ADDITIONwas added
2. 2
   ExtractionThe resulting mixture was extracted
3. 3
   Otherthe combined organic phase was evaporated to dryness under reduced pressure
4. 4
   OtherThe residue was purified by silica gel column chromatography

Procedure

To a stirred solution of nucleoside 15 (3.00 g, 4.88 mmol) in methanol (50 cm3) was added sodium methoxide (0.79 g, 14.7 mmol). The reaction mixture was stirred for 14 h at room temperature and subsequently neutralised with dilute hydrochloric acid (5 cm3) whereupon ice-cold H2O (50 cm3) was added. The resulting mixture was extracted using ethyl acetate (3×100 cm3) and the combined organic phase was evaporated to dryness under reduced pressure. The residue was purified by silica gel column chromatography using dichloromethane/methanol (98.5:1.5, v/v) as eluent to give nucleoside 16 as white solid material (2.00 g, 88%) after evaporation of the solvents under reduced pressure.

Source