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Method for synthesizing 5beta, 6beta-epoxides of steroids by a highly beta-selective epoxidation of delta5-unsaturated steroids catalyzed by ketones

Summary

A general, efficient, and environmentally friendly method is provided for producing mostly beta-epoxides of DELTA5-unsaturated steroids using certain ketones as the catalyst along with an oxidizing agent, or by using certain dioxiranes. In another aspect of the invention, a method is provided for producing mostly 5beta,6beta-epoxides of steroids from DELTA5-unsaturated steroids having a substituent at the 3alpha-position by an epoxidation reaction using a ketone along with an oxidizing agent under conditions effective to generate epoxides, or using a dioxirane under conditions effective to generate epoxides.; A whole range of DELTA5-unsaturated steroids, bearing different functional groups such as hydroxy, carbonyl, acetyl or ketal group as well as different side chains, were conveniently converted to the corresponding synthetically and biologically interesting 5beta,6beta-epoxides with excellent beta-selectivities and high yields.

Supplementary Information

Inventor: Yang, Dan | Jiao, Guan Sheng
Priority Number: US6841665B2
IPC Current: C07J007100
US Class: 540080
Assignee Applicant: The University of Hong Kong
Title: Method for synthesizing 5beta, 6beta-epoxides of steroids by a highly beta-selective epoxidation of DeltaDelta5-unsaturated steroids catalyzed by ketones | Method for synthesizing 5β, 6β-epoxides of steroids by a highly β-selective epoxidat
Usefulness: Method for synthesizing 5beta, 6beta-epoxides of steroids by a highly beta-selective epoxidation of DeltaDelta5-unsaturated steroids catalyzed by ketones | Method for synthesizing 5β, 6β-epoxides of steroids by a highly β-selective epoxidation of ΔΔ5-unsaturated steroids catalyzed by ketones
Summary: In the preparation of 5-β,6-β epoxides of steroids useful in cell proliferation regulation and cholesterol homeostasis; as probes for biochemical studies of enzymes; and as intermediates for the preparation of other oxysterols.
Novelty: Synthesis of 5-beta,6-beta epoxides of steroids useful in cell proliferation regulation involves beta-selective epoxidation of delta-5-unsaturated steroids using specified ketones or dioxiranes along with oxidizing agents

Industry

Biomedical

Sub Group

Medical Composition

Country/Region

Hong Kong

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