Methanesulfonyl chloride → Vidarabine

Participants

Reaction Steps

9-β-D-Arabinofuranosyl adenine (ara-A) is synthesized when the 3',5'-di-O-isopropylidene derivative of 9-(β-D-xylofuranosyl)adenine is treated with methanesulphonyl chloride to convert it to the corresponding 2'-O-mesyl derivative, which is cleaved by acetic acid to produce 9-(2'-O-mesyl-β-D-xylofuranosyl)adenine, which is treated with sodium methoxide in methanol to produce the 2',3'-epoxide, which is treated with sodium in aqueous dimethylformamide to open the ring and produce ara-A which is purified by crystallization.

Provenance & Evidence