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Syntheses of estetrol mqnoglucuronides
- Source :
- Steroids. 27:111-122
- Publication Year :
- 1976
- Publisher :
- Elsevier BV, 1976.
-
Abstract
- Four possible monoglucuronides of estetrol (estra-1,3,5(10)-triene-3,15 alpha, 16 alpha, 17 beta-tetraol) have been prepared from appropriately protected estetrol by the Koenigs-Knorr reaction employing cadmium carbonate as a catalyst. Condensation of methyl acetobromoglucuronate with estetrol 15,16,17-triacetate provided the 3-glucuronide acetate-methyl ester in a satisfactory yield. Introduction of the glucuronyl residue into C-17 was similarly attained by the use of estetrol 3-benzoate 15,16-acetonide. When estetrol 3,17-diacetate and acetobromosugar were stirred in anhydrous toluene in the presence of cadmium salt, the reaction occurred at C-16 and C-15 yielding two isomeric monoglucuronide derivatives in a ratio of ca. 5 to 2. Removal of the protecting groups in the four glucuronide acetate-methyl esters gave the desired estetrol glucuronides, respectively. These synthetic substrates underwent readily enzymatic hydrolysis with beef-liver beta-glucuronidase to afford estetrol.
- Subjects :
- Magnetic Resonance Spectroscopy
Chemical Phenomena
Clinical Biochemistry
Glucuronates
In Vitro Techniques
Biochemistry
Catalysis
Residue (chemistry)
chemistry.chemical_compound
Hydrolysis
Endocrinology
Enzymatic hydrolysis
Methods
Animals
Organic chemistry
Molecular Biology
Glucuronidase
Pharmacology
Estriol
Chemistry
Estetrol
Organic Chemistry
Toluene
Liver
Anhydrous
Cattle
Glucuronide
Cadmium
Subjects
Details
- ISSN :
- 0039128X
- Volume :
- 27
- Database :
- OpenAIRE
- Journal :
- Steroids
- Accession number :
- edsair.doi.dedup.....392a14e1e757a14cae0d2934ff306239