Reactions of relevance to the chemistry of aminoglycoside antibiotics. Part 13. A novel synthesis of benzyl ethers

Abstract

Benzyl ethers were prepared from alcohols by reaction with chloro(phenylmethylene)dimethylammonium chloride and sodium hydrogen telluride in sequence. The salt (1)[Me₂NC(R¹)OR²Cl^–; R¹= H, R²= cholest-5-en-3β-yl] and sodium borohydride gave the borane complex of 3β-dimethylaminomethoxycholest-5-ene. Salt (1; R¹= Ph, R²= cholest-5-en-3β-yl or 5α-cholestan-3β-yl) and ammonia or hydrazine gave the steroidal benzimidates or benzhydrazonate.