(S)-Acetoxy-cyano-((8S,9S,10R,11S,13S,14S,17S)-11-hydroxy-10,13-dimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-acetic acid methyl ester

Base Information

• Chemical Name: (S)-Acetoxy-cyano-((8S,9S,10R,11S,13S,14S,17S)-11-hydroxy-10,13-dimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-acetic acid methyl ester
• CAS No.: 130399-89-2
• Molecular Formula: C₂₅H₃₁NO₆
• Molecular Weight: 441.524

Synonyms:(S)-Acetoxy-cyano-((8S,9S,10R,11S,13S,14S,17S)-11-hydroxy-10,13-dimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-acetic acid methyl ester

Chemical Property of (S)-Acetoxy-cyano-((8S,9S,10R,11S,13S,14S,17S)-11-hydroxy-10,13-dimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-acetic acid methyl ester

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Technology Process of (S)-Acetoxy-cyano-((8S,9S,10R,11S,13S,14S,17S)-11-hydroxy-10,13-dimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-acetic acid methyl ester

There total 9 articles about (S)-Acetoxy-cyano-((8S,9S,10R,11S,13S,14S,17S)-11-hydroxy-10,13-dimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-acetic acid methyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 3.9%

methanol (67-56-1) + potassium cyanide (151-50-8) + Benzoic acid (8S,9S,10R,11S,13S,14S,17R)-11-hydroxy-17-(2-hydroxy-2-methoxy-acetyl)-10,13-dimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl ester (130399-79-0) + acetic anhydride (108-24-7) → (8S,9S,10R,11S,13S,14S)-11-Hydroxy-10,13-dimethyl-7,8,9,10,11,12,13,14,15,16-decahydro-6H-cyclopenta[a]phenanthrene-3,17-dione (898-84-0) + methyl 11β-hydroxy-3-oxo-1,4-cis-17(20)-pregnatrien-21-oate (130399-81-4) + methyl 17α-benzoyloxy-11β-hydroxy-3,20-dioxo-1,4-pregnadien-21-oate (130399-85-8) + 17α-cyano-17β-acetoxy-11β-hydroxy-1,4-androstadien-3-one (130399-80-3) + (R)-Acetoxy-cyano-((8S,9S,10R,11S,13S,14S,17S)-11-hydroxy-10,13-dimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-acetic acid methyl ester (130399-83-6) + (S)-Acetoxy-cyano-((8S,9S,10R,11S,13S,14S,17S)-11-hydroxy-10,13-dimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-acetic acid methyl ester (130399-89-2)

Guidance literature:

With pyridine; manganese(IV) oxide; acetic acid; Product distribution; Mechanism; var. time of acetylation;

DOI:10.1002/jps.2600790502

Reference yield:

Benzoic acid (8S,9S,10R,11S,13S,14S,17R)-11-hydroxy-17-(2-hydroxy-2-methoxy-acetyl)-10,13-dimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl ester (130399-79-0) → (8S,9S,10R,11S,13S,14S)-11-Hydroxy-10,13-dimethyl-7,8,9,10,11,12,13,14,15,16-decahydro-6H-cyclopenta[a]phenanthrene-3,17-dione (898-84-0) + methyl 11β-hydroxy-3-oxo-1,4-cis-17(20)-pregnatrien-21-oate (130399-81-4) + methyl 17α-benzoyloxy-11β-hydroxy-3,20-dioxo-1,4-pregnadien-21-oate (130399-85-8) + (S)-Acetoxy-cyano-((8S,9S,10R,11S,13S,14S,17S)-11-hydroxy-10,13-dimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-acetic acid methyl ester (130399-89-2)

Guidance literature:

With pyridine; potassium cyanide; manganese(IV) oxide; acetic anhydride; acetic acid; Yield given. Multistep reaction. Further byproducts given. Yields of byproduct given; 1.) MeOH, 30 min, 2.) 1 h;

DOI:10.1002/jps.2600790502

Reference yield:

methanol (67-56-1) + Benzoic acid (8S,9S,10R,11S,13S,14S,17R)-11-hydroxy-17-(2-hydroxy-2-methoxy-acetyl)-10,13-dimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl ester (130399-79-0) + acetic anhydride (108-24-7) → (8S,9S,10R,11S,13S,14S)-11-Hydroxy-10,13-dimethyl-7,8,9,10,11,12,13,14,15,16-decahydro-6H-cyclopenta[a]phenanthrene-3,17-dione (898-84-0) + methyl 11β-hydroxy-3-oxo-1,4-cis-17(20)-pregnatrien-21-oate (130399-81-4) + methyl 17α-benzoyloxy-11β-hydroxy-3,20-dioxo-1,4-pregnadien-21-oate (130399-85-8) + (S)-Acetoxy-cyano-((8S,9S,10R,11S,13S,14S,17S)-11-hydroxy-10,13-dimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-acetic acid methyl ester (130399-89-2)

Guidance literature:

With pyridine; manganese(IV) oxide; acetic acid; Yield given. Multistep reaction. Further byproducts given. Yields of byproduct given; 1.) 30 min, 2.) 1 h;

DOI:10.1002/jps.2600790502

upstream raw materials:

Benzoic acid (8S,9S,10R,11S,13S,14S,17R)-11-hydroxy-17-(2-hydroxy-2-methoxy-acetyl)-10,13-dimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl ester

methanol

potassium cyanide

acetic anhydride

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