1,1-Dimethylethyl (+/-)-(1'α,4'aβ,4'bα,8'α,8'aβ,10'β,10'aα)-dodecahydro-10'a-hydroxy-7'-(methoxycarbonyl)-1',4'a,8'a-trimethyl-6'-oxo-10'-(phenylseleno)spiro<1,3-dioxolane-2,2'-(1'H)-phenanthrene>-8'-acetate

Base Information

Chemical Name:1,1-Dimethylethyl (+/-)-(1'α,4'aβ,4'bα,8'α,8'aβ,10'β,10'aα)-dodecahydro-10'a-hydroxy-7'-(methoxycarbonyl)-1',4'a,8'a-trimethyl-6'-oxo-10'-(phenylseleno)spiro<1,3-dioxolane-2,2'-(1'H)-phenanthrene>-8'-acetate
CAS No.:91191-89-8
Molecular Formula:C₃₃H₄₆O₈Se
Molecular Weight:649.683
Hs Code.:

1,1-Dimethylethyl (+/-)-(1'α,4'aβ,4'bα,8'α,8'aβ,10'β,10'aα)-dodecahydro-10'a-hydroxy-7'-(methoxycarbonyl)-1',4'a,8'a-trimethyl-6'-oxo-10'-(phenylseleno)spiro<1,3-dioxolane-2,2'-(1'H)-phenanthrene>-8'-acetate

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Chemical Property of 1,1-Dimethylethyl (+/-)-(1'α,4'aβ,4'bα,8'α,8'aβ,10'β,10'aα)-dodecahydro-10'a-hydroxy-7'-(methoxycarbonyl)-1',4'a,8'a-trimethyl-6'-oxo-10'-(phenylseleno)spiro<1,3-dioxolane-2,2'-(1'H)-phenanthrene>-8'-acetate

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Technology Process of 1,1-Dimethylethyl (+/-)-(1'α,4'aβ,4'bα,8'α,8'aβ,10'β,10'aα)-dodecahydro-10'a-hydroxy-7'-(methoxycarbonyl)-1',4'a,8'a-trimethyl-6'-oxo-10'-(phenylseleno)spiro<1,3-dioxolane-2,2'-(1'H)-phenanthrene>-8'-acetate

There total 10 articles about 1,1-Dimethylethyl (+/-)-(1'α,4'aβ,4'bα,8'α,8'aβ,10'β,10'aα)-dodecahydro-10'a-hydroxy-7'-(methoxycarbonyl)-1',4'a,8'a-trimethyl-6'-oxo-10'-(phenylseleno)spiro<1,3-dioxolane-2,2'-(1'H)-phenanthrene>-8'-acetate 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:

: 91191-74-1
(+/-)-cis-4,4a,8,8a,9,10-Hexahydro-1,4a,8a-trimethyl-2,6-(3H,7H)-phenanthrenedione

: 91191-89-8
1,1-Dimethylethyl (+/-)-(1'α,4'aβ,4'bα,8'α,8'aβ,10'β,10'aα)-dodecahydro-10'a-hydroxy-7'-(methoxycarbonyl)-1',4'a,8'a-trimethyl-6'-oxo-10'-(phenylseleno)spiro<1,3-dioxolane-2,2'-(1'H)-phenanthrene>-8'-acetate

Guidance literature:: Multi-step reaction with 7 steps

1: 1) 2-naphthalenesulfonic acid 2) silica, water / 1) benzene, 5d, reflux 2) CH₂Cl₂, 2d, reflux

2: 97 percent / lithium, ammonia, tert-butylalcohol / tetrahydrofuran / 0.5 h

3: 1) DMF, 6h, 110 deg C 2) Et₂O, 20 min

4: 1) NaH, Phenylselenenyl chloride 2) H₂O₂ / 1) THF, a) 0 deg C b) -> 20 min, room temperature 2) CH₂Cl₂, phosphate buffer, pH 7, pyridine, a) 20 min, 0 deg C b) 19h, room temperature

5: 2) KF / 1) MeCN, 25 deg C, 5.2 kbar, 8d 2) THF, water, 7h, room temperature

6: 88 percent / m-chloroperoxybenzoic acid / CH₂Cl₂ / 0.08 h / Ambient temperature

7: 1) NaBH₄ / 1) EtOH, 1,5h, reflux 2) Et₂O

With potassium fluoride; sodium tetrahydroborate; Phenylselenyl chloride; naphthalene-2-sulfonate; ammonia; water; dihydrogen peroxide; silica gel; lithium; sodium hydride; 3-chloro-benzenecarboperoxoic acid; tert-butyl alcohol; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo00192a004

Reference yield:

: 91191-78-5
(+/-)-(1'α,4'aβ,4'bα,8'aβ)-4',4'a,4'b,5',7',8',8'a,9'-Octahydro-1',4'a,8'a-trimethylspiro<1,3-dioxolane-2,2'(1'H)-phenanthren>-6'(3'H)-one

: 91191-89-8
1,1-Dimethylethyl (+/-)-(1'α,4'aβ,4'bα,8'α,8'aβ,10'β,10'aα)-dodecahydro-10'a-hydroxy-7'-(methoxycarbonyl)-1',4'a,8'a-trimethyl-6'-oxo-10'-(phenylseleno)spiro<1,3-dioxolane-2,2'-(1'H)-phenanthrene>-8'-acetate

Guidance literature:: Multi-step reaction with 5 steps

1: 1) DMF, 6h, 110 deg C 2) Et₂O, 20 min

2: 1) NaH, Phenylselenenyl chloride 2) H₂O₂ / 1) THF, a) 0 deg C b) -> 20 min, room temperature 2) CH₂Cl₂, phosphate buffer, pH 7, pyridine, a) 20 min, 0 deg C b) 19h, room temperature

3: 2) KF / 1) MeCN, 25 deg C, 5.2 kbar, 8d 2) THF, water, 7h, room temperature

4: 88 percent / m-chloroperoxybenzoic acid / CH₂Cl₂ / 0.08 h / Ambient temperature

5: 1) NaBH₄ / 1) EtOH, 1,5h, reflux 2) Et₂O

With potassium fluoride; sodium tetrahydroborate; Phenylselenyl chloride; dihydrogen peroxide; sodium hydride; 3-chloro-benzenecarboperoxoic acid; In dichloromethane;
DOI:10.1021/jo00192a004

Reference yield:

: 91191-77-4
(+/-)-(1'α,4'aβ,8'aβ)-4',4'a,7',8',8'a,9'-Hexahydro-1',4'a,8'a-trimethylspiro<1,3-dioxolane-2,2'(1H)-phenanthren>-6'-(3'H)-one

: 91191-89-8
1,1-Dimethylethyl (+/-)-(1'α,4'aβ,4'bα,8'α,8'aβ,10'β,10'aα)-dodecahydro-10'a-hydroxy-7'-(methoxycarbonyl)-1',4'a,8'a-trimethyl-6'-oxo-10'-(phenylseleno)spiro<1,3-dioxolane-2,2'-(1'H)-phenanthrene>-8'-acetate

Guidance literature:: Multi-step reaction with 6 steps

1: 97 percent / lithium, ammonia, tert-butylalcohol / tetrahydrofuran / 0.5 h

2: 1) DMF, 6h, 110 deg C 2) Et₂O, 20 min

3: 1) NaH, Phenylselenenyl chloride 2) H₂O₂ / 1) THF, a) 0 deg C b) -> 20 min, room temperature 2) CH₂Cl₂, phosphate buffer, pH 7, pyridine, a) 20 min, 0 deg C b) 19h, room temperature

4: 2) KF / 1) MeCN, 25 deg C, 5.2 kbar, 8d 2) THF, water, 7h, room temperature

5: 88 percent / m-chloroperoxybenzoic acid / CH₂Cl₂ / 0.08 h / Ambient temperature

6: 1) NaBH₄ / 1) EtOH, 1,5h, reflux 2) Et₂O

With potassium fluoride; sodium tetrahydroborate; Phenylselenyl chloride; ammonia; dihydrogen peroxide; lithium; sodium hydride; 3-chloro-benzenecarboperoxoic acid; tert-butyl alcohol; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo00192a004