Practical Synthesis of 3β-Amino-5-Cholestene and Related 3β-Halides Involving i-Steroid and Retro-i-Steroid Rearrangements
| Autor: | Qi Sun, Sutang Cai, Blake R. Peterson |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2009 |
| Předmět: |
Hydrocarbons
Fluorinated Molecular Structure Extramural Chemistry Stereochemistry Cholestenes medicine.medical_treatment Organic Chemistry Stereoisomerism Biochemistry Cholesterylamine Combinatorial chemistry Article Steroid chemistry.chemical_compound Structure-Activity Relationship Cholestene medicine Structure–activity relationship Combinatorial Chemistry Techniques Steroids Physical and Theoretical Chemistry |
| Popis: | Derivatives of 3beta-amino-5-cholestene (3beta-cholesterylamine) are of substantial interest as cellular probes and have potential medicinal applications. However, existing syntheses of 3beta-amino-5-cholestene are of limited preparative utility. We report here a practical method for the stereoselective preparation of 3beta-amino-5-cholestene, 3beta-chloro-5-cholestene, 3beta-bromo-5-cholestene, and 3beta-iodo-5-cholestene from inexpensive cholesterol. A sequential i-steroid/retro-i-steroid rearrangement promoted by boron trifluoride etherate and trimethylsilyl azide converted cholest-5-en-3beta-ol methanesulfonate to 3beta-azido-cholest-5-ene with retention of configuration in 93% yield. |
| Databáze: | OpenAIRE |
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