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Synthesis of Novel Mannose-based Crown Ethers

Rathjens A., Thiem J.

Polish Journal of Chemistry

2005

Vol. 79 / nr 2

211-222

Anovel class of chiral crown ether analogues incorporating carbohydrate subunits can be easily prepared from methyl _-D-mannopyranoside. By a short reaction sequence involving either alkylations using a dibutylstannane intermediate or by phase transfer catalyzed etherification well defined disaccharide mimetics were obtained, which are suitable starting materials in Richman-Atkins cyclizations. The combination of several various reaction partners led to structurally interesting ring systems differing in ring size, number of carbon and hetero atoms (20-40) as well as kind of sugar subunits.