(5S,6R,8S,11R,13S,14S,17R)-11-(4-Dimethylamino-phenyl)-3,3-dimethoxy-6,13-dimethyl-17-[3-(tetrahydro-pyran-2-yloxy)-propyl]-1,2,3,4,6,7,8,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthrene-5,17-diol

Base Information

Chemical Name:(5S,6R,8S,11R,13S,14S,17R)-11-(4-Dimethylamino-phenyl)-3,3-dimethoxy-6,13-dimethyl-17-[3-(tetrahydro-pyran-2-yloxy)-propyl]-1,2,3,4,6,7,8,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthrene-5,17-diol
CAS No.:148676-91-9
Molecular Formula:C₃₇H₅₇NO₆
Molecular Weight:611.863
Hs Code.:

(5S,6R,8S,11R,13S,14S,17R)-11-(4-Dimethylamino-phenyl)-3,3-dimethoxy-6,13-dimethyl-17-[3-(tetrahydro-pyran-2-yloxy)-propyl]-1,2,3,4,6,7,8,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthrene-5,17-diol

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Chemical Property of (5S,6R,8S,11R,13S,14S,17R)-11-(4-Dimethylamino-phenyl)-3,3-dimethoxy-6,13-dimethyl-17-[3-(tetrahydro-pyran-2-yloxy)-propyl]-1,2,3,4,6,7,8,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthrene-5,17-diol

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Technology Process of (5S,6R,8S,11R,13S,14S,17R)-11-(4-Dimethylamino-phenyl)-3,3-dimethoxy-6,13-dimethyl-17-[3-(tetrahydro-pyran-2-yloxy)-propyl]-1,2,3,4,6,7,8,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthrene-5,17-diol

There total 9 articles about (5S,6R,8S,11R,13S,14S,17R)-11-(4-Dimethylamino-phenyl)-3,3-dimethoxy-6,13-dimethyl-17-[3-(tetrahydro-pyran-2-yloxy)-propyl]-1,2,3,4,6,7,8,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthrene-5,17-diol 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:

: 148676-90-8
3,3-dimethoxy-11β-<4-(dimethylamino)phenyl>-6β-methyl-17α-(3-tetrahydropyranyloxy-1-propynyl)estr-9-ene-5α,17β-diol

: 148676-91-9
(5S,6R,8S,11R,13S,14S,17R)-11-(4-Dimethylamino-phenyl)-3,3-dimethoxy-6,13-dimethyl-17-[3-(tetrahydro-pyran-2-yloxy)-propyl]-1,2,3,4,6,7,8,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthrene-5,17-diol

Guidance literature:: With hydrogen; palladium on barium sulfate; In ethanol; toluene;
DOI:10.1002/recl.19931120206

Reference yield:

: 118968-54-0
6β-methylestra-5(10),9(11)-diene-3,17-dione

: 148676-91-9
(5S,6R,8S,11R,13S,14S,17R)-11-(4-Dimethylamino-phenyl)-3,3-dimethoxy-6,13-dimethyl-17-[3-(tetrahydro-pyran-2-yloxy)-propyl]-1,2,3,4,6,7,8,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthrene-5,17-diol

Guidance literature:: Multi-step reaction with 5 steps

1: 69 percent / malonic acid / 6 h / Ambient temperature

2: 1) ethylmagnesium bromide / 1) THF, 0.5 h, r.t., 2) THF, 3 h

3: 47 percent / NaHCO₃, 80percent 3-chloroperoxybenzoic acid / CH₂Cl₂ / 3 h / -10 - 0 °C

4: 71 percent / CuCl / tetrahydrofuran / 3 h / Ambient temperature

5: H₂ / 5percent Pd-BaSO₄ / toluene; ethanol

With malonic acid; ethylmagnesium bromide; hydrogen; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; copper(l) chloride; palladium on barium sulfate; In tetrahydrofuran; ethanol; dichloromethane; toluene;
DOI:10.1002/recl.19931120206

Reference yield:

: 118968-46-0
6β-methylestra-5(10),9(11)-diene-3,17-dione 3,17-bis(1,2-ethanediyl acetal)

: 148676-91-9
(5S,6R,8S,11R,13S,14S,17R)-11-(4-Dimethylamino-phenyl)-3,3-dimethoxy-6,13-dimethyl-17-[3-(tetrahydro-pyran-2-yloxy)-propyl]-1,2,3,4,6,7,8,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthrene-5,17-diol

Guidance literature:: Multi-step reaction with 6 steps

1: 99 percent / 70percent aqueous acetic acid / 1 h / 50 °C

2: 69 percent / malonic acid / 6 h / Ambient temperature

3: 1) ethylmagnesium bromide / 1) THF, 0.5 h, r.t., 2) THF, 3 h

4: 47 percent / NaHCO₃, 80percent 3-chloroperoxybenzoic acid / CH₂Cl₂ / 3 h / -10 - 0 °C

5: 71 percent / CuCl / tetrahydrofuran / 3 h / Ambient temperature

6: H₂ / 5percent Pd-BaSO₄ / toluene; ethanol

With malonic acid; ethylmagnesium bromide; hydrogen; sodium hydrogencarbonate; acetic acid; 3-chloro-benzenecarboperoxoic acid; copper(l) chloride; palladium on barium sulfate; In tetrahydrofuran; ethanol; dichloromethane; toluene;
DOI:10.1002/recl.19931120206