(R)-2-[(1R,2R,4aS,8aS)-5-(4-Methoxy-benzyloxymethyl)-1,2,4a-trimethyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-yl]-1-((S)-2-vinyl-oxiranyl)-ethanol

Base Information

Chemical Name:(R)-2-[(1R,2R,4aS,8aS)-5-(4-Methoxy-benzyloxymethyl)-1,2,4a-trimethyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-yl]-1-((S)-2-vinyl-oxiranyl)-ethanol
CAS No.:214413-33-9
Molecular Formula:C₂₈H₄₀O₄
Molecular Weight:440.623
Hs Code.:

Synonyms:(R)-2-[(1R,2R,4aS,8aS)-5-(4-Methoxy-benzyloxymethyl)-1,2,4a-trimethyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-yl]-1-((S)-2-vinyl-oxiranyl)-ethanol

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Chemical Property of (R)-2-[(1R,2R,4aS,8aS)-5-(4-Methoxy-benzyloxymethyl)-1,2,4a-trimethyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-yl]-1-((S)-2-vinyl-oxiranyl)-ethanol

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Technology Process of (R)-2-[(1R,2R,4aS,8aS)-5-(4-Methoxy-benzyloxymethyl)-1,2,4a-trimethyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-yl]-1-((S)-2-vinyl-oxiranyl)-ethanol

There total 9 articles about (R)-2-[(1R,2R,4aS,8aS)-5-(4-Methoxy-benzyloxymethyl)-1,2,4a-trimethyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-yl]-1-((S)-2-vinyl-oxiranyl)-ethanol 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: 86.0%

: 214413-20-4
(R)-1-[(1R,2R,4aS,8aS)-5-(4-Methoxy-benzyloxymethyl)-1,2,4a-trimethyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-yl]-3-methylene-pent-4-en-2-ol

: 214413-33-9
(R)-2-[(1R,2R,4aS,8aS)-5-(4-Methoxy-benzyloxymethyl)-1,2,4a-trimethyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-yl]-1-((S)-2-vinyl-oxiranyl)-ethanol

: (R)-2-[(1R,2R,4aS,8aS)-5-(4-Methoxy-benzyloxymethyl)-1,2,4a-trimethyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-yl]-1-((R)-2-vinyl-oxiranyl)-ethanol

Guidance literature:: With titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2S,3S)-tartrate; In dichloromethane; at -20 ℃;
DOI:10.1021/jo981331l

Reference yield:

: 218453-51-1
Trifluoro-methanesulfonic acid (4aS,5R,6R,8aS)-5,6,8a-trimethyl-5-(2-triisopropylsilanyloxy-ethyl)-3,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl ester

: 214413-33-9
(R)-2-[(1R,2R,4aS,8aS)-5-(4-Methoxy-benzyloxymethyl)-1,2,4a-trimethyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-yl]-1-((S)-2-vinyl-oxiranyl)-ethanol

Guidance literature:: Multi-step reaction with 7 steps

1.1: 88 percent / LiCl; Bu₃SnH / Pd(PPh₃)4 / tetrahydrofuran / 4 h / 50 °C

2.1: 9-BBN / tetrahydrofuran / 2 h / 0 °C

2.2: 89 percent / NaOH; H₂O₂ / methanol

3.1: 83 percent / NaH; Bu₄NI / dimethylformamide / 6 h / 25 °C

4.1: 98 percent / TBAF*THF / 2 h / 25 °C

5.1: 91 percent / PCC/Celite / CH₂Cl₂ / 1.5 h / 25 °C

6.1: 71 percent / molecular sieves / toluene / 72 h / -78 °C

7.1: 86 percent / D-(-)-diethyl tartrate; Ti(i-PrO)4; tBuOOH / CH₂Cl₂ / -20 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; 9-borabicyclo[3.3.1]nonane dimer; molecular sieve; diethyl (2S,3S)-tartrate; Celite; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; tetra-(n-butyl)ammonium iodide; sodium hydride; pyridinium chlorochromate; lithium chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; 1.1: Hydroformylation / 2.1: Addition / 2.2: Oxidation / 3.1: Etherification / 4.1: Hydrolysis / 5.1: Oxidation / 6.1: Substitution / 7.1: Oxidation;
DOI:10.1021/jo981331l

Reference yield:

: 214413-28-2
(4aS,5R,6R,8aS)-5,6,8a-Trimethyl-5-(2-triisopropylsilanyloxy-ethyl)-octahydro-naphthalen-1-one

: 214413-33-9
(R)-2-[(1R,2R,4aS,8aS)-5-(4-Methoxy-benzyloxymethyl)-1,2,4a-trimethyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-yl]-1-((S)-2-vinyl-oxiranyl)-ethanol

Guidance literature:: Multi-step reaction with 8 steps

1.1: 100 percent / NaHMDS / tetrahydrofuran / 1 h / -78 °C

2.1: 88 percent / LiCl; Bu₃SnH / Pd(PPh₃)4 / tetrahydrofuran / 4 h / 50 °C

3.1: 9-BBN / tetrahydrofuran / 2 h / 0 °C

3.2: 89 percent / NaOH; H₂O₂ / methanol

4.1: 83 percent / NaH; Bu₄NI / dimethylformamide / 6 h / 25 °C

5.1: 98 percent / TBAF*THF / 2 h / 25 °C

6.1: 91 percent / PCC/Celite / CH₂Cl₂ / 1.5 h / 25 °C

7.1: 71 percent / molecular sieves / toluene / 72 h / -78 °C

8.1: 86 percent / D-(-)-diethyl tartrate; Ti(i-PrO)4; tBuOOH / CH₂Cl₂ / -20 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; 9-borabicyclo[3.3.1]nonane dimer; molecular sieve; diethyl (2S,3S)-tartrate; Celite; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; sodium hexamethyldisilazane; tetra-(n-butyl)ammonium iodide; sodium hydride; pyridinium chlorochromate; lithium chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; 1.1: Esterification / 2.1: Hydroformylation / 3.1: Addition / 3.2: Oxidation / 4.1: Etherification / 5.1: Hydrolysis / 6.1: Oxidation / 7.1: Substitution / 8.1: Oxidation;
DOI:10.1021/jo981331l