Synthesis of 15 alpha-hydroxyestrogen 15-N-acetylglucosaminides.
Steroids
; 60(3): 277-84, 1995 Mar.
Article
em En
| MEDLINE
| ID: mdl-7792832
ABSTRACT
The synthesis of 15-N-acetylglucosaminides of 15 alpha-hydroxyesterone, 15 alpha-hydroxyestradiol, and 15 alpha-hydroxyestriol (estetrol) is described. The latter two were prepared by condensation of 2-acetamido-1 alpha-chloro-1,2-dideoxy-3,4,6-trio-O-acetyl-D-glucopyranose with appropriately protected 15 alpha-hydroxyestrogens by the Koenigs-Knorr reaction employing cadmium carbonate as a catalyst. Subsequent removal of protecting groups with methanolic potassium hydroxide provided the desired conjugates. 15 alpha-Hydroxyestrone 15-N-acetylglucosaminide was synthesized from the corresponding 15 alpha-hydroxyestradiol derivative by Jones oxidation followed by brief alkaline hydrolysis. These conjugates underwent enzymatic hydrolysis with beta-N-acetylglucosaminidase from Jack beans to produce 15 alpha-hydroxyestrogens.
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Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Estradiol
/
Estriol
/
Estrona
/
Glucosamina
Idioma:
En
Revista:
Steroids
Ano de publicação:
1995
Tipo de documento:
Article
País de afiliação:
Japão