title: Novel approach to the preparation of hemisuccinates of steroids bearing tertiary alcohol group.
abstract: 17β-O-Hemisuccinates of typical representatives of Anabolic-Androgenic Steroids, 17β-hydroxy-17-methylandrostan-4-en-3-one, 17β-hydroxy-17-methyl-2-oxa-5α-androstan-3-one, 17β-hydroxy-17-methyl-5α-androstano-[3,2-c]pyrazole, were prepared. Several methods for the hemisuccinate preparation were tested. The indirect method using 1-ethyl-3-(dimethylaminopropyl)carbodiimide coupling reagent to form an ester bond of steroid with 2-(trimethylsilyl)ethyl hydrogen butanedioate was finally applied. Using the selectively removable protecting group, the desired hemisuccinates of steroids bearing tertiary alcohol group were obtained.
authors: Institute of Chemical Technology, Faculty of Food and Biochemical Technology, Department of Chemistry of Natural Compounds, Technická 5, 16628 Prague 6, Czech Republic.
authors: Ondřej
authors: O
authors: Longin
authors: Institute of Organic Chemistry and Biochemistry AS CR, v.v.i., Flemingovo nám. 2, 16610 Prague 6, Czech Republic.
authors: Ivan
authors: I
authors: Černý
authors: Institute of Chemical Technology, Faculty of Food and Biochemical Technology, Department of Chemistry of Natural Compounds, Technická 5, 16628 Prague 6, Czech Republic. Electronic address: drasarp@vscht.cz.
authors: Pavel
authors: P
authors: Drašar
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D015394:Molecular Structure; D013256:Steroids / Q000737:chemistry*; D013386:Succinates / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000438:Alcohols; D013256:Steroids; D013386:Succinates
keywords: Anabolic–Androgenic Steroid; Ester formation; Hemisuccinate; Tertiary alcohol