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2005
Carbohydrates
U 0500
Synthesis of Some 1,4-Oxazepanes Fused with 1,6-Anhydro-β-D-hexopyranoses.
3,11,13-Trioxa-7-azatricyclo[8.2.1.02,8]tridecane Derivatives. — β-D-Altropyra12- 203 nose
(V), the common intermediate for the syntheses of oxazepanes (VII), (IX), (XI),
(XII), and (XIII), is obtained from β-D-galactopyranose (I) by a non-optimized
five-step synthesis in 48% overall yield. Standard procedures such as acetylation, methylation, deacetylation as well as an Eschweiler—Clark methylation, cf. (V)→(VII),
furnish the corresponding oxazepanes. Ammonium salt (IX) is devoid of activity at
muscarinic M3 receptors. — (TRTEK, T.; CERNY, M.; TRNKA, T.; BUDESINSKY*,
M.; CISAROVA, I.; Collect. Czech. Chem. Commun. 69 (2004) 9, 1818-1828; Inst.
Org. Chem. Biochem., Acad. Sci. Czech Rep., CZ-166 10 Prague 6, Czech Republic;
Eng.) — H. Hoennerscheid
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