(1S,4aS,5R,6R,8S,8aS)-(-)-decahydro-1-[3-(t-butyldimethylsiloxy)propyl]-5-[2-(t-butyldiphenylsiloxy)ethyl]-1-hydroxy-5,6,8a-trimethyl-8-trimethylsilylnaphthalene

Base Information

• Chemical Name: (1S,4aS,5R,6R,8S,8aS)-(-)-decahydro-1-[3-(t-butyldimethylsiloxy)propyl]-5-[2-(t-butyldiphenylsiloxy)ethyl]-1-hydroxy-5,6,8a-trimethyl-8-trimethylsilylnaphthalene
• CAS No.: 199525-13-8
• Molecular Formula: C₄₃H₇₄O₃Si₃
• Molecular Weight: 723.315

Synonyms:(1S,4aS,5R,6R,8S,8aS)-(-)-decahydro-1-[3-(t-butyldimethylsiloxy)propyl]-5-[2-(t-butyldiphenylsiloxy)ethyl]-1-hydroxy-5,6,8a-trimethyl-8-trimethylsilylnaphthalene

Chemical Property of (1S,4aS,5R,6R,8S,8aS)-(-)-decahydro-1-[3-(t-butyldimethylsiloxy)propyl]-5-[2-(t-butyldiphenylsiloxy)ethyl]-1-hydroxy-5,6,8a-trimethyl-8-trimethylsilylnaphthalene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,4aS,5R,6R,8S,8aS)-(-)-decahydro-1-[3-(t-butyldimethylsiloxy)propyl]-5-[2-(t-butyldiphenylsiloxy)ethyl]-1-hydroxy-5,6,8a-trimethyl-8-trimethylsilylnaphthalene

There total 15 articles about (1S,4aS,5R,6R,8S,8aS)-(-)-decahydro-1-[3-(t-butyldimethylsiloxy)propyl]-5-[2-(t-butyldiphenylsiloxy)ethyl]-1-hydroxy-5,6,8a-trimethyl-8-trimethylsilylnaphthalene 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%

tert-butyldimethylsilyl chloride (18162-48-6) + (1S,4aS,5R,6R,8S,8aS)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-1-(3-hydroxy-propyl)-5,6,8a-trimethyl-8-trimethylsilanyl-decahydro-naphthalen-1-ol (199525-25-2) → (1S,4aS,5R,6R,8S,8aS)-(-)-decahydro-1-[3-(t-butyldimethylsiloxy)propyl]-5-[2-(t-butyldiphenylsiloxy)ethyl]-1-hydroxy-5,6,8a-trimethyl-8-trimethylsilylnaphthalene (199525-13-8)

Guidance literature:

With 2,6-dimethylpyridine; dmap; In dichloromethane; at 23 ℃; for 12h;

DOI:10.1021/ja973023v

Reference yield:

(4aS)-1,4aβ-dimethyl-4,4a,7,8-tetrahydronaphthalene-2,5(3H,6H)-dione-5-ethyeneacetal (26742-33-6) → (1S,4aS,5R,6R,8S,8aS)-(-)-decahydro-1-[3-(t-butyldimethylsiloxy)propyl]-5-[2-(t-butyldiphenylsiloxy)ethyl]-1-hydroxy-5,6,8a-trimethyl-8-trimethylsilylnaphthalene (199525-13-8)

Guidance literature:

Multi-step reaction with 15 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

With 2,6-dimethylpyridine; dmap; sodium tetrahydroborate; sodium periodate; sodium dihydrogenphosphate; methanesulfonamide; dimethylsulfide borane complex; 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 / 13.1: Grignard reaction / 14.1: hydroboration / 14.2: Oxidation / 15.1: silylation;

DOI:10.1021/ja973023v

Reference yield:

(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) (91547-51-2) → (1S,4aS,5R,6R,8S,8aS)-(-)-decahydro-1-[3-(t-butyldimethylsiloxy)propyl]-5-[2-(t-butyldiphenylsiloxy)ethyl]-1-hydroxy-5,6,8a-trimethyl-8-trimethylsilylnaphthalene (199525-13-8)

Guidance literature:

Multi-step reaction with 14 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

With 2,6-dimethylpyridine; dmap; sodium tetrahydroborate; sodium periodate; sodium dihydrogenphosphate; methanesulfonamide; dimethylsulfide borane complex; 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 / 12.1: Grignard reaction / 13.1: hydroboration / 13.2: Oxidation / 14.1: silylation;

DOI:10.1021/ja973023v

upstream raw materials:

tert-butyldimethylsilyl chloride

(1S,4aS,5R,6R,8S,8aS)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-1-(3-hydroxy-propyl)-5,6,8a-trimethyl-8-trimethylsilanyl-decahydro-naphthalen-1-ol

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

(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)

Downstream raw materials:

(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

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

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

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