Synthesis of 2-hydroxyestriol monoglucuronides and monosulfates.

Abstract:

:The ring A monoglucuronides and monosulfates of 2-hydroxyestriol were synthesized from 2-hydroxyestriol 16,17-diacetate by means of the Koenigs-Knorr reaction with methyl alpha-acetobromoglucuronate and sulfation with sulfur trioxide-pyridine complex, respectively. The conjugated positions of these compounds were definitely established by conversion to 2-hydroxyestriol monomethyl ethers by methylation, then enzymatic hydrolysis. The ring D monoglucuronides and monosulfates of 2-hydroxyestriol were also prepared from 2-hydroxyestriol 2,3-dibenzyl ether by glucuronidation and sulfation in a similar fashion followed by debenzylation, respectively. The positions of conjugation were established on the basis of their 1H-nuclear magnetic resonance spectral data.

journal_name

Steroids

journal_title

Steroids

authors

Ohkubo T,Wakasawa T,Nambara T

doi

10.1016/0039-128x(90)90009-z

subject

Has Abstract

pub_date

1990-03-01 00:00:00

pages

128-32

issue

3

eissn

0039-128X

issn

1878-5867

pii

0039-128X(90)90009-Z

journal_volume

55

pub_type

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