2735-20-8

Upstream product

• 1912-53-4 6-nitrocholest-5-ene 
• 1061-78-5 6-oxo-5α-cholestan-3β-yl acetate oxime 
• 1912-53-4 (10R,13R,17R)-17-((R)-1,5-Dimethyl-hexyl)-10,13-dimethyl-6-nitro-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene 
• 108-24-7 acetic anhydride 
• 570-74-1 cholest-5-ene 
• 2735-32-2 6-nitroimino-5α-cholestane 
• 570-46-7 5α-cholestan-6-one 

Downstream Products

• 570-46-7 5α-cholestan-6-one 
• 2735-32-2 6-nitroimino-5α-cholestane 
• 63866-18-2 7-oxa-B-homo-5α-cholestan-6-one 
• 570-46-7 (5S,10R,13R,17R)-17-((R)-1,5-Dimethyl-hexyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-6-one 
• 2735-32-2 5-α-cholestan-6-nitrimine 

Relevant academic research and scientific papers

Construction of novel steroidal isoxazolidinone derivatives under Vilsmeier-Haack conditions

A novel expeditious and convenient synthesis of 5α-cholestano-[5,6-c] -isoxazolidin-5′-ones based on the reaction of 5α-6- hydroxyiminocholestanes with Vilsmeier-Haack reagent (DMF/POCl3) is described. The systems presented here, are novel scaffolds and have not been described before. Structural assignment of newly synthesized compounds was performed by IR, 1H NMR, 13C NMR, 2D 1H- 1H COSY, MS and analytical data.

Reduction of Steroidal Nitroolefins with Zinc-Acetic Acid without Added Water

Zinc-acetic acid reduction (without added water) of steroidal nitroolefins (I-III) leads to the formation of respective N-acetylated enamines (X-XII) alongwith the parent ketones (IV-VI) and the oximes (VII-IX).These products have been identified on the basis of their spectral properties and by comparison with authentic samples where available.

Thermolytic Transformation of Steroidal Nitroimines

Thermolysis of 6-nitroimino-5α-cholestan-3β-yl acetate (I), 6-nitroimino-5α-cholestane (VII) and 7-nitroiminocholest-5-en-3β-yl chloride (XII) in refluxing xylene affords a mixture of products in the case of I and VII and a chlorine-free product in the case of XII.The known products have been characterized by direct comparison while unknown products by elemental analyses and spectral data.

A Novel Method for Preparation of Steroidal Ketoximes from Nitroolefins

Steroidal 6-nitroolefins (I-IV) undergo facile reaction with NH3-MeOH-Zn yielding exclusively the corresponding 6-one oximes (V-VIII) in quantitative yields.The method appears to be of general applicability.