60385-81-1

Usage

InChI:InChI=1/C19H26O4/c1-18-6-5-14-13(15(18)9-16(22)17(18)23)3-2-11-8-12(21)4-7-19(11,14)10-20/h8,13-16,20,22H,2-7,9-10H2,1H3/t13-,14+,15+,16-,18+,19-/m1/s1

Upstream product

• 116535-61-6 16α-bromo-6β,19-oxido-4-androstene-3,17-dione 
• 116535-60-5 5α,16α-dibromo-6β,19-epoxyandrostane-3,17-dione 
• 99714-90-6 5α,16α-dibromo-3β-hydroxy-6β,19-epoxyandrostan-17-one 
• 7745-16-6 5α-bromo-3β-hydroxy-6β,19-epoxyandrostan-17-one 
• 116535-62-7 16α-hydroxy-6β,19-epoxyandrost-4-ene-3,17-dione 

Relevant academic research and scientific papers

Synthesis of 16α,19-dihydroxy-4-androstene-3,17-dione and 3β,16α,19-trihydroxy-5-androsten-17-one and their 17β-hydroxy-16-keto isomers

3β,16α,19-Trihydroxy-5-androsten-17-one [6] and 16α,19-dihydroxy-4-androstene-3,17-dione [14] were synthesized from the 5α-bromo-6β,19-epoxy-17-ketone derivative 1, using the bromination at C-16α of the 17-ketone 1 and the controlled alkaline hydrolysis of the 16α-bromo-17-ketones 2 and 11 as key reactions. Zinc dust reductive cleavage of the 6β,19-epoxy-16α-hydroxy-17-ketones 4 and 12, produced by controlled hydrolysis, gave the corresponding 19-alcohol derivatives 6 and 14, which were rearranged to the 17β-hydroxy-16-ketones 7 and 15 when treated with sodium hydroxide. The 3β,16α,17β,19-tetrol 8 was obtained from the 16α-ketol 6 by reaction with sodium borohydride.