(4aS,5R,6R,8S,8aS)-(-)-3,4,4a,5,6,7,8,8a-octahydro-5-(2-t-butyldiphenylsiloxyethyl)-5,6,8a-trimethyl-8-trimethylsilylnaphthalen-1(2H)-one

Base Information

Chemical Name:(4aS,5R,6R,8S,8aS)-(-)-3,4,4a,5,6,7,8,8a-octahydro-5-(2-t-butyldiphenylsiloxyethyl)-5,6,8a-trimethyl-8-trimethylsilylnaphthalen-1(2H)-one
CAS No.:199525-12-7
Molecular Formula:C₃₄H₅₂O₂Si₂
Molecular Weight:548.957
Hs Code.:

Synonyms:(4aS,5R,6R,8S,8aS)-(-)-3,4,4a,5,6,7,8,8a-octahydro-5-(2-t-butyldiphenylsiloxyethyl)-5,6,8a-trimethyl-8-trimethylsilylnaphthalen-1(2H)-one

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Chemical Property of (4aS,5R,6R,8S,8aS)-(-)-3,4,4a,5,6,7,8,8a-octahydro-5-(2-t-butyldiphenylsiloxyethyl)-5,6,8a-trimethyl-8-trimethylsilylnaphthalen-1(2H)-one

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Technology Process of (4aS,5R,6R,8S,8aS)-(-)-3,4,4a,5,6,7,8,8a-octahydro-5-(2-t-butyldiphenylsiloxyethyl)-5,6,8a-trimethyl-8-trimethylsilylnaphthalen-1(2H)-one

There total 12 articles about (4aS,5R,6R,8S,8aS)-(-)-3,4,4a,5,6,7,8,8a-octahydro-5-(2-t-butyldiphenylsiloxyethyl)-5,6,8a-trimethyl-8-trimethylsilylnaphthalen-1(2H)-one 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: 76.0%

: 199525-23-0
(4aS,5S,8S,8aS)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-5,8a-dimethyl-6-methylene-8-trimethylsilanyl-octahydro-naphthalen-1-one

: 199525-12-7
(4aS,5R,6R,8S,8aS)-(-)-3,4,4a,5,6,7,8,8a-octahydro-5-(2-t-butyldiphenylsiloxyethyl)-5,6,8a-trimethyl-8-trimethylsilylnaphthalen-1(2H)-one

: (4aS,5R,6S,8S,8aS)-(-)-3,4,4a,5,6,7,8,8a-octahydro-5-(2-t-butyldiphenylsiloxyethyl)-5,6,8a-trimethyl-8-trimethylsilylnaphthalen-1(2H)-one

Guidance literature:: Wilkinson's catalyst; In benzene; at 65 ℃; for 23h; under 51714.8 Torr;
DOI:10.1021/ja973023v

Reference yield:

: 26742-33-6
(4aS)-1,4aβ-dimethyl-4,4a,7,8-tetrahydronaphthalene-2,5(3H,6H)-dione-5-ethyeneacetal

: 199525-12-7
(4aS,5R,6R,8S,8aS)-(-)-3,4,4a,5,6,7,8,8a-octahydro-5-(2-t-butyldiphenylsiloxyethyl)-5,6,8a-trimethyl-8-trimethylsilylnaphthalen-1(2H)-one

Guidance literature:: Multi-step reaction with 12 steps

1.1: lithium; water / liquid ammonia; tetrahydrofuran / 0.17 h / -40 °C

1.2: 82 percent / isoprene / liquid ammonia; tetrahydrofuran / 1.5 h / -78 - -35 °C

2.1: lithium diisopropylamide / tetrahydrofuran; hexamethylphosphoric acid triamide / 0.67 h / -78 - 23 °C

2.2: tetrahydrofuran; hexamethylphosphoric acid triamide / 0.33 h / 0 - 23 °C

3.1: m-chloroperbenzoic acid; NaH₂PO₄ / CH₂Cl₂ / 2 h / -78 °C

4.1: 747 mg / trimethyl phosphite / benzene / 13 h / 90 °C

5.1: methyllithium / diethyl ether; hexamethylphosphoric acid triamide / -78 - 0 °C

5.2: 64 percent / diethyl ether; hexamethylphosphoric acid triamide / 3 h / -78 °C

6.1: 97 percent / dimethylsulfoxide / 2 h / 23 °C

7.1: 97 percent / potassium ferricyanide; potassium carbonate; methanesulfonamide / DHQD₂-PYDZ; potassium osmate(VI) dihydrate / 2-methyl-propan-2-ol; H₂O / 4.25 h / 0 - 23 °C

8.1: sodium periodate / tetrahydrofuran; H₂O / 0.5 h / 23 °C

9.1: 795 mg / sodium borohydride / tetrahydrofuran; ethanol / 0.33 h / 0 °C

10.1: 100 percent / pyridinium p-toluenesulfonate / acetone; H₂O / 2 h / 65 °C

11.1: 96 percent / 2,6-lutidine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 1.5 h / 23 °C

12.1: 76 percent / tris(triphenylphosphine)rhodium chloride / benzene / 23 h / 65 °C / 51714.8 Torr

With 2,6-dimethylpyridine; dmap; sodium tetrahydroborate; sodium periodate; sodium dihydrogenphosphate; methanesulfonamide; water; methyllithium; pyridinium p-toluenesulfonate; lithium; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; potassium hexacyanoferrate(III); lithium diisopropyl amide; phosphorous acid trimethyl ester; potassium osmate(VI); Wilkinson's catalyst; (DHQD)₂PYDZ; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; ethanol; dichloromethane; ammonia; water; dimethyl sulfoxide; acetone; tert-butyl alcohol; benzene; 1.1: Reduction / 1.2: Alkylation / 2.1: Metallation / 2.2: phenylsulfenation / 3.1: Oxidation / 4.1: Elimination / 5.1: Metallation / 5.2: Addition / 6.1: Wittig methylenation / 7.1: dihydroxylation / 8.1: Oxidation / 9.1: Reduction / 10.1: deketalization / 11.1: silylation / 12.1: Hydrogenation;
DOI:10.1021/ja973023v

Reference yield:

: 91547-51-2
(4aS,5S,8aS)-(+)-3,4,4a,7,8,8a-Hexahydro-5,8a-dimethyl-5-(prop-2-enyl)naphthalene-1,6(2H,5H)-dione 1-(Ethylene Acetal)

: 199525-12-7
(4aS,5R,6R,8S,8aS)-(-)-3,4,4a,5,6,7,8,8a-octahydro-5-(2-t-butyldiphenylsiloxyethyl)-5,6,8a-trimethyl-8-trimethylsilylnaphthalen-1(2H)-one

Guidance literature:: Multi-step reaction with 11 steps

1.1: lithium diisopropylamide / tetrahydrofuran; hexamethylphosphoric acid triamide / 0.67 h / -78 - 23 °C

1.2: tetrahydrofuran; hexamethylphosphoric acid triamide / 0.33 h / 0 - 23 °C

2.1: m-chloroperbenzoic acid; NaH₂PO₄ / CH₂Cl₂ / 2 h / -78 °C

3.1: 747 mg / trimethyl phosphite / benzene / 13 h / 90 °C

4.1: methyllithium / diethyl ether; hexamethylphosphoric acid triamide / -78 - 0 °C

4.2: 64 percent / diethyl ether; hexamethylphosphoric acid triamide / 3 h / -78 °C

5.1: 97 percent / dimethylsulfoxide / 2 h / 23 °C

6.1: 97 percent / potassium ferricyanide; potassium carbonate; methanesulfonamide / DHQD₂-PYDZ; potassium osmate(VI) dihydrate / 2-methyl-propan-2-ol; H₂O / 4.25 h / 0 - 23 °C

7.1: sodium periodate / tetrahydrofuran; H₂O / 0.5 h / 23 °C

8.1: 795 mg / sodium borohydride / tetrahydrofuran; ethanol / 0.33 h / 0 °C

9.1: 100 percent / pyridinium p-toluenesulfonate / acetone; H₂O / 2 h / 65 °C

10.1: 96 percent / 2,6-lutidine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 1.5 h / 23 °C

11.1: 76 percent / tris(triphenylphosphine)rhodium chloride / benzene / 23 h / 65 °C / 51714.8 Torr

With 2,6-dimethylpyridine; dmap; sodium tetrahydroborate; sodium periodate; sodium dihydrogenphosphate; methanesulfonamide; methyllithium; pyridinium p-toluenesulfonate; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; potassium hexacyanoferrate(III); lithium diisopropyl amide; phosphorous acid trimethyl ester; potassium osmate(VI); Wilkinson's catalyst; (DHQD)₂PYDZ; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; ethanol; dichloromethane; water; dimethyl sulfoxide; acetone; tert-butyl alcohol; benzene; 1.1: Metallation / 1.2: phenylsulfenation / 2.1: Oxidation / 3.1: Elimination / 4.1: Metallation / 4.2: Addition / 5.1: Wittig methylenation / 6.1: dihydroxylation / 7.1: Oxidation / 8.1: Reduction / 9.1: deketalization / 10.1: silylation / 11.1: Hydrogenation;
DOI:10.1021/ja973023v