2-[(1S,3R,3aR,3bS,6R,6aR,6bR)-3-(2-Methoxy-ethoxymethoxy)-3a,6-dimethyl-decahydro-cyclobutadicyclopenten-1-yl]-2-phenylselanyl-malonic acid dimethyl ester

Base Information

Chemical Name:2-[(1S,3R,3aR,3bS,6R,6aR,6bR)-3-(2-Methoxy-ethoxymethoxy)-3a,6-dimethyl-decahydro-cyclobutadicyclopenten-1-yl]-2-phenylselanyl-malonic acid dimethyl ester
CAS No.:89165-87-7
Molecular Formula:C₂₇H₃₈O₇Se
Molecular Weight:553.555
Hs Code.:

2-[(1S,3R,3aR,3bS,6R,6aR,6bR)-3-(2-Methoxy-ethoxymethoxy)-3a,6-dimethyl-decahydro-cyclobutadicyclopenten-1-yl]-2-phenylselanyl-malonic acid dimethyl ester

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Chemical Property of 2-[(1S,3R,3aR,3bS,6R,6aR,6bR)-3-(2-Methoxy-ethoxymethoxy)-3a,6-dimethyl-decahydro-cyclobutadicyclopenten-1-yl]-2-phenylselanyl-malonic acid dimethyl ester

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Technology Process of 2-[(1S,3R,3aR,3bS,6R,6aR,6bR)-3-(2-Methoxy-ethoxymethoxy)-3a,6-dimethyl-decahydro-cyclobutadicyclopenten-1-yl]-2-phenylselanyl-malonic acid dimethyl ester

There total 14 articles about 2-[(1S,3R,3aR,3bS,6R,6aR,6bR)-3-(2-Methoxy-ethoxymethoxy)-3a,6-dimethyl-decahydro-cyclobutadicyclopenten-1-yl]-2-phenylselanyl-malonic acid dimethyl 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:

: 930-30-3
cyclopent-2-enone

: 89165-87-7,132294-36-1
2-[(1S,3R,3aR,3bS,6R,6aR,6bR)-3-(2-Methoxy-ethoxymethoxy)-3a,6-dimethyl-decahydro-cyclobutadicyclopenten-1-yl]-2-phenylselanyl-malonic acid dimethyl ester

Guidance literature:: Multi-step reaction with 13 steps

1: 50.5 percent / pentane / 100 h / Irradiation

2: 1.) MeLi / 1.) THF, 20 deg C, 2 h, 2.) 20 deg C, 15 h

3: 96.3 percent / SO₂ / 2 h / Ambient temperature

4: 1.) n-BuLi / 1.) THF, hexane, RT, 20 min, 2.) -78 deg C, 1 h

5: 96.3 percent / toluene / 5 h / Heating

6: 94.7 percent / H₂, PtO₂ / ethyl acetate / 1 h

7: 82.6 percent / 34percent CH₃COOOH / acetic acid / 48 h / Ambient temperature

8: 40percent aq. KOH / methanol / 6 h / Heating

9: diethyl ether

10: 89 percent / i-Pr₂NEt / CH₂Cl₂ / 72 h / Ambient temperature

11: 1.) LDA, α,α'-dipyridyl / 1.) THF, hexane, -78 deg C, 15 min, 2.) from -78 deg C to RT, 1 h

12: diethyl ether

13: 1.) LDA, α,α'-dipyridyl / 1.) THF, -78 deg C, 30 min, 2.) from -78 deg C to RT, 1 h

With peracetic acid; [2,2]bipyridinyl; platinum(IV) oxide; potassium hydroxide; n-butyllithium; sulfur dioxide; methyllithium; hydrogen; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; In methanol; diethyl ether; dichloromethane; acetic acid; ethyl acetate; toluene; pentane;
DOI:10.1021/ja00008a043

Reference yield:

: 89165-82-2,89177-42-4
6-methyl-2-<(trimethylsilyl)oxy>bicyclo<2.2.1>hept-5-ene-2-carbonitriles

: 89165-87-7,132294-36-1
2-[(1S,3R,3aR,3bS,6R,6aR,6bR)-3-(2-Methoxy-ethoxymethoxy)-3a,6-dimethyl-decahydro-cyclobutadicyclopenten-1-yl]-2-phenylselanyl-malonic acid dimethyl ester

Guidance literature:: Multi-step reaction with 13 steps

1: 50.5 percent / pentane / 100 h / Irradiation

2: 1.) MeLi / 1.) THF, 20 deg C, 2 h, 2.) 20 deg C, 15 h

3: 96.3 percent / SO₂ / 2 h / Ambient temperature

4: 1.) n-BuLi / 1.) THF, hexane, RT, 20 min, 2.) -78 deg C, 1 h

5: 96.3 percent / toluene / 5 h / Heating

6: 94.7 percent / H₂, PtO₂ / ethyl acetate / 1 h

7: 82.6 percent / 34percent CH₃COOOH / acetic acid / 48 h / Ambient temperature

8: 40percent aq. KOH / methanol / 6 h / Heating

9: diethyl ether

10: 89 percent / i-Pr₂NEt / CH₂Cl₂ / 72 h / Ambient temperature

11: 1.) LDA, α,α'-dipyridyl / 1.) THF, hexane, -78 deg C, 15 min, 2.) from -78 deg C to RT, 1 h

12: diethyl ether

13: 1.) LDA, α,α'-dipyridyl / 1.) THF, -78 deg C, 30 min, 2.) from -78 deg C to RT, 1 h

With peracetic acid; [2,2]bipyridinyl; platinum(IV) oxide; potassium hydroxide; n-butyllithium; sulfur dioxide; methyllithium; hydrogen; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; In methanol; diethyl ether; dichloromethane; acetic acid; ethyl acetate; toluene; pentane;
DOI:10.1021/ja00008a043

Reference yield:

: 89165-83-3
C₁₄H₁₈O

: 89165-87-7,132294-36-1
2-[(1S,3R,3aR,3bS,6R,6aR,6bR)-3-(2-Methoxy-ethoxymethoxy)-3a,6-dimethyl-decahydro-cyclobutadicyclopenten-1-yl]-2-phenylselanyl-malonic acid dimethyl ester

Guidance literature:: Multi-step reaction with 11 steps

1: 96.3 percent / SO₂ / 2 h / Ambient temperature

2: 1.) n-BuLi / 1.) THF, hexane, RT, 20 min, 2.) -78 deg C, 1 h

3: 96.3 percent / toluene / 5 h / Heating

4: 94.7 percent / H₂, PtO₂ / ethyl acetate / 1 h

5: 82.6 percent / 34percent CH₃COOOH / acetic acid / 48 h / Ambient temperature

6: 40percent aq. KOH / methanol / 6 h / Heating

7: diethyl ether

8: 89 percent / i-Pr₂NEt / CH₂Cl₂ / 72 h / Ambient temperature

9: 1.) LDA, α,α'-dipyridyl / 1.) THF, hexane, -78 deg C, 15 min, 2.) from -78 deg C to RT, 1 h

10: diethyl ether

11: 1.) LDA, α,α'-dipyridyl / 1.) THF, -78 deg C, 30 min, 2.) from -78 deg C to RT, 1 h

With peracetic acid; [2,2]bipyridinyl; platinum(IV) oxide; potassium hydroxide; n-butyllithium; sulfur dioxide; hydrogen; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; In methanol; diethyl ether; dichloromethane; acetic acid; ethyl acetate; toluene;
DOI:10.1021/ja00008a043