75220-37-0

Usage

InChI:InChI=1/C21H28O4/c1-20-8-7-17-15(16(20)4-5-18(20)19(25)11-22)3-2-13-10-14(24)6-9-21(13,17)12-23/h10,12,15-18,22H,2-9,11H2,1H3/t15-,16-,17-,18+,20-,21+/m0/s1

Upstream product

• 104494-65-7 19-t-butyldimethylsilyloxyprogesterone 
• 104494-64-6 1-[(3S,8S,9S,10S,13S,14S,17S)-10-(tert-Butyl-dimethyl-silanyloxymethyl)-3-hydroxy-13-methyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-ethanone 
• 31751-06-1 (3S,8R,9S,10S,13S,14S)-3-Hydroxy-13-methyl-10-(tetrahydro-pyran-2-yloxymethyl)-1,2,3,4,7,8,9,10,11,12,13,14,15,16-tetradecahydro-cyclopenta[a]phenanthren-17-one 
• 2685-64-5 5-bromo-6β,19-oxido-3β-hydroxy-5α-androstan-17-one 3-acetate 
• 6901-40-2 19,21-dihydroxypregn-4-ene-3,20-dione 21-acetate 
• 4229-69-0 3β-acetoxy-5-bromo-6β-hydroxy-5α-androstan-17-one 
• 2723-07-1 5-Bromo-6β-hydroxy-20-oxo-5α-pregnan-3β-yl acetate 
• 853-23-6 prasterone acetate 
• 2857-42-3 3β-acetoxy-19-hydroxyandrost-5-en-17-one 
• 1778-02-5 Pregnenolone acetate 
• 26360-40-7 3β-acetoxy-19-hydroxy-Δ5-pregnen-20-one 
• 88378-35-2 19-oxo-11-deoxycorticosterone acetate 
• 104494-72-6 t-butyl 3β-t-butyldimethylsilyloxy-19-(2-tetrahydropyranyloxy)-20-methoxypregna-5,17(20)-dien-21-oate 
• 104494-70-4 methyl 3β-t-butyldimethylsilyloxy-19-(2-tetrahidropyranyloxy)-20-methoxypregna-5,17(20)-dien-21-oate 

Relevant academic research and scientific papers

Process for the synthesis of the hydroxyacetyl side-chain of steroids of the pregnane type, novel 21-hydroxy-20-oxo-17α-pregnane compounds and pharmaceutical preparations containing them

The present invention relates to a novel general process for synthesizing a α- or β-oriented hydroxyacetyl side chain of steroids of the pregnane type, which comprises treating a corresponding steroid carbaldehyde in succession with formaldehyde dimethylmercaptal-S-oxide in the form of an alkali metal salt thereof, and with a strongly acid hydrolysing agent.Preferred final products are compounds of the formula STR1 wherein n is 1 or 2, R 2 represents methyl or difluoromethyl, and R 1 represents hydroxymethyl, methoxymethyl, acetoxymethyl or hydrogen, and, if n is 2 and/or R 2 is difluoromethyl, R 1 also represents methyl. These compounds act as agonists or antagonists of natural steroid hormones. The antigestagenic 19,21-dihydroxy-17α-pregn-4-ene-3,20-dione and its 6,7-dehydro derivatives and diacetates are of particular interest.