Acetic Anhydride → HCID 54086996, compound

Participants

Reaction Steps

By substituting 9.5 ml. of acetic anhydride for the propionic anhydride in paragraph 1 (a) and using 200 ml. of dry pyridine, the product obtained by the procedure of paragraph 1 a) is 9-(2,3-di-O-acetyl-5O-(tert-butyldimethylsily)-β-D-arabinofuranosyl)adenine, which, on reaction with 31.3 g. of tetrabutylammonium fluoride in 300 ml. of tetrahydrofuran, following the procedure of paragraph 1 (b), gives 9-(3,5-di-O-acetyl-β-D-arabinofuranosyl)adenine. By substituting 23.4 ml. of butyryl chloride for the propionic anhydride in paragraph 1 (a) and using 17.9 g. of the silyl ether in 250 ml. of pyridine, the product obtained is 9-(2,3-di-O-butyryl-5-O-(tert-butyldimethylsilyl)-β-D-arabinofuranosyl) adenine, which on reaction with 37 g. of tetrabutylammonium fluoride in 350 ml. of tetrahydrofuran following the procedure of paragraph 1 (b) gives 9-(3,5-di-O-butyryl-β-D-arabinofuranosyl)adenine.

Provenance & Evidence