23457-40-1

Usage

InChI:InChI=1/C19H28O4/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/h2,12-16,20-22H,3-10H2,1H3/t12?,13-,14+,15+,16?,18+,19-/m1/s1

Upstream product

• 116535-58-1 5α-bromo-3β,16α-dihydroxy-6β,19-oxidoandrostan-17-one 
• 2857-45-6 3β,19-dihydroxy-5-androsten-17-one 
• 23457-47-8 Acetic acid (3S,8R,9S,10S,13S,14S)-3,17-diacetoxy-13-methyl-1,2,3,4,7,8,9,11,12,13,14,15-dodecahydro-cyclopenta[a]phenanthren-10-ylmethyl ester 
• 23457-46-7 Acetic acid (3S,8R,9S,10S,13S,14S,16R)-3-acetoxy-16-bromo-13-methyl-17-oxo-1,2,3,4,7,8,9,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-10-ylmethyl ester 
• 2685-64-5 5-bromo-6β,19-oxido-3β-hydroxy-5α-androstan-17-one 3-acetate 
• 2857-44-5 3β,19-O,O'-diacetyl-19-hydroxydehydroepiandrosterone 
• 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 
• 23457-45-6 (3S,8R,9S,10S,13S,14S,16R)-10-Hydroxymethyl-17,17-dimethoxy-13-methyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,16-diol 

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.