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.

journal_name

Steroids

journal_title

Steroids

authors

Schwarz S,Thieme I,Richter M,Undeutsch B,Henkel H,Elger W

doi

10.1016/s0039-128x(96)00200-0

subject

Has Abstract

pub_date

1996-12-01 00:00:00

pages

710-7

issue

12

eissn

0039-128X

issn

1878-5867

pii

S0039-128X(96)00200-0

journal_volume

61

pub_type

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