(3Z,5E)-6-[(3S,8S,9S,10R,13S,14S,17R)-10,13-Dimethyl-3-(tetrahydro-pyran-2-yloxy)-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

Base Information

Chemical Name:(3Z,5E)-6-[(3S,8S,9S,10R,13S,14S,17R)-10,13-Dimethyl-3-(tetrahydro-pyran-2-yloxy)-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
CAS No.:84051-55-8
Molecular Formula:C₃₈H₅₄O₃S
Molecular Weight:590.911
Hs Code.:

(3Z,5E)-6-[(3S,8S,9S,10R,13S,14S,17R)-10,13-Dimethyl-3-(tetrahydro-pyran-2-yloxy)-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

Synonyms:(3Z,5E)-6-[(3S,8S,9S,10R,13S,14S,17R)-10,13-Dimethyl-3-(tetrahydro-pyran-2-yloxy)-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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Chemical Property of (3Z,5E)-6-[(3S,8S,9S,10R,13S,14S,17R)-10,13-Dimethyl-3-(tetrahydro-pyran-2-yloxy)-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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Technology Process of (3Z,5E)-6-[(3S,8S,9S,10R,13S,14S,17R)-10,13-Dimethyl-3-(tetrahydro-pyran-2-yloxy)-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

There total 8 articles about (3Z,5E)-6-[(3S,8S,9S,10R,13S,14S,17R)-10,13-Dimethyl-3-(tetrahydro-pyran-2-yloxy)-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 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: 73.0%

: 84051-51-4
(E)-(S)-2-[(3S,8S,9S,10R,13S,14S,17S)-10,13-Dimethyl-3-(tetrahydro-pyran-2-yloxy)-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

: 84051-55-8
(3Z,5E)-6-[(3S,8S,9S,10R,13S,14S,17R)-10,13-Dimethyl-3-(tetrahydro-pyran-2-yloxy)-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

Guidance literature:: With nickel dichloride; In water; tert-butyl alcohol; at 60 ℃; for 24h;
DOI:10.1021/ja00341a051

Reference yield: 73.0%

: 84051-51-4
(E)-2-[(3S,8S,9S,10R,13S,14S,17S)-10,13-Dimethyl-3-(tetrahydro-pyran-2-yloxy)-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

: 84051-55-8
(3Z,5E)-6-[(3S,8S,9S,10R,13S,14S,17R)-10,13-Dimethyl-3-(tetrahydro-pyran-2-yloxy)-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

Guidance literature:: With nickel dichloride; In water; tert-butyl alcohol; at 60 ℃; for 26h;
DOI:10.1021/jo00180a025

Reference yield:

: 78905-13-2
phenyl 1-(trimethylsilyl)prop-2-en-1-yl sulfide

: 84051-55-8
(3Z,5E)-6-[(3S,8S,9S,10R,13S,14S,17R)-10,13-Dimethyl-3-(tetrahydro-pyran-2-yloxy)-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

Guidance literature:: Multi-step reaction with 3 steps

1: 57 percent / 1.) sec-BuLi / 1.) THF-HMPA, -78 deg C

2: 54 percent / 1.) sec-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 °C / 1.) THF-HMPA, -78 deg C, 2.) 0 deg C

3: 73 percent / NiCl₂ / 2-methyl-propan-2-ol; H₂O / 24 h / 60 °C

With sec.-butyllithium; nickel dichloride; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; water; tert-butyl alcohol;
DOI:10.1021/ja00341a051