title: Synthesis of estrogen sulfamates: compounds with a novel endocrinological profile.
abstract: Estrogen sulfamates are promising hormones by oral administration. Therefore, generally applicable and convenient methods for the multigram synthesis of these derivatives are desirable. Numerous estra-1,3,5(10)-trienes derived from estrone, estradiol. 14 alpha,15 alpha-methylenestradiol, ethinylestradiol, and estriol have been esterified with sulfamoyl chloride and N-methylsulfamoyl chloride by a novel approach involving the use of 2,6-di-tert-butylpyridines as bases and chemoselective hydroxy group protections. These pathways circumvent the nonselective formation of esters and side reactions by in situ generated azasulfenes. For toxicological and clinical studies a new synthesis of estrone sulfamate on a 100-g scale was developed using dimethylformamide as the solvent and base.
authors.affiliation: Division of Research and Development, Jenapharm GmbH, Jena, Germany.
authors.forename: S
authors.initials: S
authors.lastname: Schwarz
authors.forename: I
authors.initials: I
authors.lastname: Thieme
authors.forename: M
authors.initials: M
authors.lastname: Richter
authors.forename: B
authors.initials: B
authors.lastname: Undeutsch
authors.forename: H
authors.initials: H
authors.lastname: Henkel
authors.forename: W
authors.initials: W
authors.lastname: Elger
mesh_terms: D004958:Estradiol / Q000031:analogs & derivatives / Q000737:chemistry; D004964:Estriol / Q000031:analogs & derivatives / Q000737:chemistry; D004967:Estrogens / Q000138:chemical synthesis* / Q000737:chemistry; D004970:Estrone / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D013451:Sulfonic Acids / Q000737:chemistry*
chemical_list: D004967:Estrogens; D013451:Sulfonic Acids; D004970:Estrone; D004958:Estradiol; C005741:sulfamic acid; D004964:Estriol