(1S,4aS,5R,6R)-(-)-1,2,3,4,4a,5,6,7-octahydro-5-[2-(t-butyldiphenylsiloxy)ethyl]-1-(4-methyl-4-pentenyl)-1,5,6-trimethylnaphthalene

Base Information

Chemical Name:(1S,4aS,5R,6R)-(-)-1,2,3,4,4a,5,6,7-octahydro-5-[2-(t-butyldiphenylsiloxy)ethyl]-1-(4-methyl-4-pentenyl)-1,5,6-trimethylnaphthalene
CAS No.:199525-15-0
Molecular Formula:C₃₇H₅₄OSi
Molecular Weight:542.921
Hs Code.:

Synonyms:(1S,4aS,5R,6R)-(-)-1,2,3,4,4a,5,6,7-octahydro-5-[2-(t-butyldiphenylsiloxy)ethyl]-1-(4-methyl-4-pentenyl)-1,5,6-trimethylnaphthalene

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Chemical Property of (1S,4aS,5R,6R)-(-)-1,2,3,4,4a,5,6,7-octahydro-5-[2-(t-butyldiphenylsiloxy)ethyl]-1-(4-methyl-4-pentenyl)-1,5,6-trimethylnaphthalene

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Technology Process of (1S,4aS,5R,6R)-(-)-1,2,3,4,4a,5,6,7-octahydro-5-[2-(t-butyldiphenylsiloxy)ethyl]-1-(4-methyl-4-pentenyl)-1,5,6-trimethylnaphthalene

There total 18 articles about (1S,4aS,5R,6R)-(-)-1,2,3,4,4a,5,6,7-octahydro-5-[2-(t-butyldiphenylsiloxy)ethyl]-1-(4-methyl-4-pentenyl)-1,5,6-trimethylnaphthalene 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: 97.0%

: 557-93-7
2-bromoprop-1-ene

: 199525-29-6
tert-Butyl-{2-[(1R,2R,5S,8aS)-5-(3-iodo-propyl)-1,2,5-trimethyl-1,2,3,5,6,7,8,8a-octahydro-naphthalen-1-yl]-ethoxy}-diphenyl-silane

: 199525-15-0
(1S,4aS,5R,6R)-(-)-1,2,3,4,4a,5,6,7-octahydro-5-[2-(t-butyldiphenylsiloxy)ethyl]-1-(4-methyl-4-pentenyl)-1,5,6-trimethylnaphthalene

Guidance literature:: 2-bromoprop-1-ene; With tert.-butyl lithium; In diethyl ether; pentane; at -78 - 23 ℃; for 1.5h;

With copper(l) iodide; In diethyl ether; pentane; at -78 - -40 ℃; for 1h;

tert-Butyl-{2-[(1R,2R,5S,8aS)-5-(3-iodo-propyl)-1,2,5-trimethyl-1,2,3,5,6,7,8,8a-octahydro-naphthalen-1-yl]-ethoxy}-diphenyl-silane; In diethyl ether; pentane; at -78 - 0 ℃; for 0.5h;
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

: 199525-15-0
(1S,4aS,5R,6R)-(-)-1,2,3,4,4a,5,6,7-octahydro-5-[2-(t-butyldiphenylsiloxy)ethyl]-1-(4-methyl-4-pentenyl)-1,5,6-trimethylnaphthalene

Guidance literature:: Multi-step reaction with 18 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

13.1: 99 percent / diethyl ether / 0.33 h / -78 - 23 °C

14.1: borane-dimethyl sulfide complex / diethyl ether / 2.5 h / -78 - 23 °C

14.2: 95 percent / aq. NaOH; aq. H₂O₂ / diethyl ether; ethanol / 3.5 h / 0 - 23 °C

15.1: 97 percent / 2,6-lutidine; DMAP / CH₂Cl₂ / 12 h / 23 °C

16.1: boron trifluoride / CH₂Cl₂ / 3 h / -78 °C

16.2: 70 percent / pyridinium p-toluenesulfonate / ethanol / 2.5 h / 55 °C

17.1: 97 percent / iodine; triphenylphosphine; imidazole / CH₂Cl₂ / 0.17 h / 23 °C

18.1: t-butyllithium / pentane; diethyl ether / 1.5 h / -78 - 23 °C

18.2: copper(I) iodide / pentane; diethyl ether / 1 h / -78 - -40 °C

18.3: 97 percent / pentane; diethyl ether / 0.5 h / -78 - 0 °C

With 1H-imidazole; 2,6-dimethylpyridine; dmap; sodium tetrahydroborate; sodium periodate; sodium dihydrogenphosphate; methanesulfonamide; dimethylsulfide borane complex; boron trifluoride; water; methyllithium; iodine; tert.-butyl lithium; pyridinium p-toluenesulfonate; lithium; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; 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; pentane; 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 / 13.1: Grignard reaction / 14.1: hydroboration / 14.2: Oxidation / 15.1: silylation / 16.1: Rearrangement / 16.2: desilylation / 17.1: Iodination / 18.1: Metallation / 18.2: transmetallation / 18.3: Sub;
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)

: 199525-15-0
(1S,4aS,5R,6R)-(-)-1,2,3,4,4a,5,6,7-octahydro-5-[2-(t-butyldiphenylsiloxy)ethyl]-1-(4-methyl-4-pentenyl)-1,5,6-trimethylnaphthalene

Guidance literature:: Multi-step reaction with 17 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

12.1: 99 percent / diethyl ether / 0.33 h / -78 - 23 °C

13.1: borane-dimethyl sulfide complex / diethyl ether / 2.5 h / -78 - 23 °C

13.2: 95 percent / aq. NaOH; aq. H₂O₂ / diethyl ether; ethanol / 3.5 h / 0 - 23 °C

14.1: 97 percent / 2,6-lutidine; DMAP / CH₂Cl₂ / 12 h / 23 °C

15.1: boron trifluoride / CH₂Cl₂ / 3 h / -78 °C

15.2: 70 percent / pyridinium p-toluenesulfonate / ethanol / 2.5 h / 55 °C

16.1: 97 percent / iodine; triphenylphosphine; imidazole / CH₂Cl₂ / 0.17 h / 23 °C

17.1: t-butyllithium / pentane; diethyl ether / 1.5 h / -78 - 23 °C

17.2: copper(I) iodide / pentane; diethyl ether / 1 h / -78 - -40 °C

17.3: 97 percent / pentane; diethyl ether / 0.5 h / -78 - 0 °C

With 1H-imidazole; 2,6-dimethylpyridine; dmap; sodium tetrahydroborate; sodium periodate; sodium dihydrogenphosphate; methanesulfonamide; dimethylsulfide borane complex; boron trifluoride; methyllithium; iodine; tert.-butyl lithium; pyridinium p-toluenesulfonate; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; 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; pentane; 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 / 12.1: Grignard reaction / 13.1: hydroboration / 13.2: Oxidation / 14.1: silylation / 15.1: Rearrangement / 15.2: desilylation / 16.1: Iodination / 17.1: Metallation / 17.2: transmetallation / 17.3: Substitution;
DOI:10.1021/ja973023v