(E)-2-((3S,8S,9S,10R,13S,14S,17S)-3-Methoxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-6-methyl-5-phenylsulfanyl-hepta-3,5-dien-2-ol

Base Information

• Chemical Name: (E)-2-((3S,8S,9S,10R,13S,14S,17S)-3-Methoxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-6-methyl-5-phenylsulfanyl-hepta-3,5-dien-2-ol
• CAS No.: 84051-53-6
• Molecular Formula: C₃₄H₄₈O₂S
• Molecular Weight: 520.82

Synonyms:(E)-2-((3S,8S,9S,10R,13S,14S,17S)-3-Methoxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-6-methyl-5-phenylsulfanyl-hepta-3,5-dien-2-ol

Chemical Property of (E)-2-((3S,8S,9S,10R,13S,14S,17S)-3-Methoxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-6-methyl-5-phenylsulfanyl-hepta-3,5-dien-2-ol

Chemical Property:

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Technology Process of (E)-2-((3S,8S,9S,10R,13S,14S,17S)-3-Methoxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-6-methyl-5-phenylsulfanyl-hepta-3,5-dien-2-ol

There total 3 articles about (E)-2-((3S,8S,9S,10R,13S,14S,17S)-3-Methoxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-6-methyl-5-phenylsulfanyl-hepta-3,5-dien-2-ol 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: 39.0%

(Z)-2-((3S,8S,9S,10R,13S,14S,17S)-3-Methoxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-5-phenylsulfanyl-5-trimethylsilanyl-pent-4-en-2-ol (88930-44-3,83862-55-9) + acetone (67-64-1) → (E)-2-((3S,8S,9S,10R,13S,14S,17S)-3-Methoxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-6-methyl-5-phenylsulfanyl-hepta-3,5-dien-2-ol (84051-53-6)

Guidance literature:

With sec.-butyllithium; 1.) HMPA-THF, -78 deg C, 1 h, 2.) 0 deg C;

DOI:10.1021/ja00341a051

Reference yield:

pregnenolone methyl ether (511-26-2) → (E)-2-((3S,8S,9S,10R,13S,14S,17S)-3-Methoxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-6-methyl-5-phenylsulfanyl-hepta-3,5-dien-2-ol (84051-53-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 59 percent / 1.) sec-BuLi / 1.) THF-HMPA, -78 deg C

2: 39 percent / sec-BuLi / 1.) HMPA-THF, -78 deg C, 1 h, 2.) 0 deg C

With sec.-butyllithium;

DOI:10.1021/ja00341a051

Reference yield:

phenyl 1-(trimethylsilyl)prop-2-en-1-yl sulfide (78905-13-2) → (E)-2-((3S,8S,9S,10R,13S,14S,17S)-3-Methoxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-6-methyl-5-phenylsulfanyl-hepta-3,5-dien-2-ol (84051-53-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 59 percent / 1.) sec-BuLi / 1.) THF-HMPA, -78 deg C

2: 39 percent / sec-BuLi / 1.) HMPA-THF, -78 deg C, 1 h, 2.) 0 deg C

With sec.-butyllithium;

DOI:10.1021/ja00341a051

upstream raw materials:

(Z)-2-((3S,8S,9S,10R,13S,14S,17S)-3-Methoxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-5-phenylsulfanyl-5-trimethylsilanyl-pent-4-en-2-ol

acetone

pregnenolone methyl ether

phenyl 1-(trimethylsilyl)prop-2-en-1-yl sulfide

Downstream raw materials:

(3S,8S,9S,10R,13S,14S,17R)-17-((1E,3Z)-5-Ethoxy-1,5-dimethyl-4-phenylsulfanyl-hexa-1,3-dienyl)-3-methoxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene

(3S,8S,9S,10R,13S,14S,17R)-17-((1Z,3Z)-5-Ethoxy-1,5-dimethyl-4-phenylsulfanyl-hexa-1,3-dienyl)-3-methoxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene

(3Z,5Z)-6-((3S,8S,9S,10R,13S,14S,17R)-3-Methoxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2-methyl-3-phenylsulfanyl-hepta-3,5-dien-2-ol

(3Z,5E)-6-((3S,8S,9S,10R,13S,14S,17R)-3-Methoxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2-methyl-3-phenylsulfanyl-hepta-3,5-dien-2-ol

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