5837-39-8

Upstream product

• 70223-10-8 6-ketocholestanol 
• 74-88-4 methyl iodide 
• 75-77-4 chloro-trimethyl-silane 
• 127460-91-7 (3S,8S,9S,10R,13R,14S,17R)-3-methoxy-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)-6-nitro-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene 
• 85249-15-6 6α-hydroxy-3β-methoxy-5α-cholestane 
• 149-73-5 trimethyl orthoformate 
• 1174-92-1 cholesteryl methyl ether 
• 85198-21-6 3β-methoxy-4-cholesten-6α-ol 

Downstream Products

• 103721-15-9 Toluene-4-sulfonic acid 2-[(3S,5S,6R,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-3-methoxy-6,10,13-trimethyl-hexadecahydro-cyclopenta[a]phenanthren-6-yloxy]-ethyl ester 
• 116329-76-1 C₄₃H₆₁NO₃ 
• 116329-75-0 3β-methoxy-6β-(3'-benzoylphenyl)acetamidocholestane 

Relevant academic research and scientific papers

Recation of Nitro-alkenes with Iodotrimethylsilane: A New Method for the Conversion of Vinyl Nitrosteroids to Ketosteroids

Iodotrimethylsilane generated in situ from chlorotrimethylsilane and sodium iodide effects the reduction of nitro-alkenes (1a-e) and (5) at -5 to O deg C to furnish the ketones (2a-e) and (6) respectively as the major products.

Preparation and Cleavage Reactions of Some Steroidal Epoxides

The steroidal epoxides (12), (13), (28), and (34) have been prepared and their reactions investigated.Attempts to prepare the epoxides (12) and (13) by the action of dimethylsulphonium methyilde or dimethylsulphoxonium methylide on the ketone 1 gave instead the rearranged product (2) and its methyl ether (3).Compound (2) has also been obtained by base-catalysed isomerization of the spiro-epoxide (13).Lewis acid-catalysed rearrangement of epoxides (12), (28), and (34) into the A-homo-B-norsteroids (16), (29), and (43) respectively is described.

Aspects of the Reduction of Double Bond Using Cob(I)alamin as Catalyst

The olefinic system in 3β-methoxy-4-cholesten-6α-ol (2) is reduced using cob(I)alamin (1(I); see Scheme 1) as catalyst; aqueous acetic acid as solvent and metallic zinc as electron source (cf.Schemes 2 and 3).Experimental evidence for an attack of 1(I) on both faces of the double bond is presented.By the same catalyst (1R)-10,10-dimethyl-2-pinene-10-carbonitrile (9) is first transformed to the menthene derivative 11 (see Schemes 4 and 5).The ring opening is then followed by a fast saturation of the disubstituted olefinic system in 11, and ultimately the remaining double bond is reduced in a slow reaction.The cis-configurated saturated menthane derivative 16 is the main final product (16/17 ca. 10:1).