(R)-2-{(4'R,4'aS,8'R,8'aR)-4'-[(S)-2-(4-Methoxy-benzyloxy)-1-methyl-ethyl]-6'-methyl-3',4',4'a,7',8',8'a-hexahydro-1'H-spiro[[1,3]dioxolane-2,2'-naphthalen]-8'-yl}-3-methyl-butan-1-ol

Base Information

• Chemical Name: (R)-2-{(4'R,4'aS,8'R,8'aR)-4'-[(S)-2-(4-Methoxy-benzyloxy)-1-methyl-ethyl]-6'-methyl-3',4',4'a,7',8',8'a-hexahydro-1'H-spiro[[1,3]dioxolane-2,2'-naphthalen]-8'-yl}-3-methyl-butan-1-ol
• CAS No.: 583866-26-6
• Molecular Formula: C₂₉H₄₄O₅
• Molecular Weight: 472.665
• Mol file: 583866-26-6.mol

Synonyms:(R)-2-{(4'R,4'aS,8'R,8'aR)-4'-[(S)-2-(4-Methoxy-benzyloxy)-1-methyl-ethyl]-6'-methyl-3',4',4'a,7',8',8'a-hexahydro-1'H-spiro[[1,3]dioxolane-2,2'-naphthalen]-8'-yl}-3-methyl-butan-1-ol

Chemical Property of (R)-2-{(4'R,4'aS,8'R,8'aR)-4'-[(S)-2-(4-Methoxy-benzyloxy)-1-methyl-ethyl]-6'-methyl-3',4',4'a,7',8',8'a-hexahydro-1'H-spiro[[1,3]dioxolane-2,2'-naphthalen]-8'-yl}-3-methyl-butan-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-{(4'R,4'aS,8'R,8'aR)-4'-[(S)-2-(4-Methoxy-benzyloxy)-1-methyl-ethyl]-6'-methyl-3',4',4'a,7',8',8'a-hexahydro-1'H-spiro[[1,3]dioxolane-2,2'-naphthalen]-8'-yl}-3-methyl-butan-1-ol

There total 3 articles about (R)-2-{(4'R,4'aS,8'R,8'aR)-4'-[(S)-2-(4-Methoxy-benzyloxy)-1-methyl-ethyl]-6'-methyl-3',4',4'a,7',8',8'a-hexahydro-1'H-spiro[[1,3]dioxolane-2,2'-naphthalen]-8'-yl}-3-methyl-butan-1-ol 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: 100.0%

tert-Butyl-((R)-2-{(4'R,4'aS,8'R,8'aR)-4'-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-6'-methyl-3',4',4'a,7',8',8'a-hexahydro-1'H-spiro[[1,3]dioxolane-2,2'-naphthalen]-8'-yl}-3-methyl-butoxy)-dimethyl-silane (583866-25-5) → (R)-2-{(4'R,4'aS,8'R,8'aR)-4'-[(S)-2-(4-Methoxy-benzyloxy)-1-methyl-ethyl]-6'-methyl-3',4',4'a,7',8',8'a-hexahydro-1'H-spiro[[1,3]dioxolane-2,2'-naphthalen]-8'-yl}-3-methyl-butan-1-ol (583866-26-6)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 14h;

DOI:10.1021/jo0301301

Reference yield:

(1S,2S,4S,8R)-2-[(1E,3S)-4-(p-methoxybenzyloxy)-3-methyl-1-butenyl]-8-[(1R)-1-[(tert-butyldimethylsiloxy)methyl]-2-methylpropyl]-1-methylbicyclo[2.2.2]oct-5-en-2-ol (583866-64-2) → (R)-2-{(4'R,4'aS,8'R,8'aR)-4'-[(S)-2-(4-Methoxy-benzyloxy)-1-methyl-ethyl]-6'-methyl-3',4',4'a,7',8',8'a-hexahydro-1'H-spiro[[1,3]dioxolane-2,2'-naphthalen]-8'-yl}-3-methyl-butan-1-ol (583866-26-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 72 percent / 18-crown-6; potassium hexamethyldisilazide / tetrahydrofuran; toluene / 1 h / 120 °C / sealed tube

2: 84 percent / p-toluenesulfonic acid / benzene / 4 h / Heating

3: 100 percent / TBAF / tetrahydrofuran / 14 h / 20 °C

With 18-crown-6 ether; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; toluene-4-sulfonic acid; In tetrahydrofuran; toluene; benzene;

DOI:10.1021/jo0301301

Reference yield:

(4R,4aS,8R,8aR)-8-[(R)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-2-methyl-propyl]-4-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-6-methyl-3,4,4a,7,8,8a-hexahydro-1H-naphthalen-2-one (583866-24-4) → (R)-2-{(4'R,4'aS,8'R,8'aR)-4'-[(S)-2-(4-Methoxy-benzyloxy)-1-methyl-ethyl]-6'-methyl-3',4',4'a,7',8',8'a-hexahydro-1'H-spiro[[1,3]dioxolane-2,2'-naphthalen]-8'-yl}-3-methyl-butan-1-ol (583866-26-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 84 percent / p-toluenesulfonic acid / benzene / 4 h / Heating

2: 100 percent / TBAF / tetrahydrofuran / 14 h / 20 °C

With tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; In tetrahydrofuran; benzene;

DOI:10.1021/jo0301301

upstream raw materials:

tert-Butyl-((R)-2-{(4'R,4'aS,8'R,8'aR)-4'-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-6'-methyl-3',4',4'a,7',8',8'a-hexahydro-1'H-spiro[[1,3]dioxolane-2,2'-naphthalen]-8'-yl}-3-methyl-butoxy)-dimethyl-silane

(4R,4aS,8R,8aR)-8-[(R)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-2-methyl-propyl]-4-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-6-methyl-3,4,4a,7,8,8a-hexahydro-1H-naphthalen-2-one

(1S,2S,4S,8R)-2-[(1E,3S)-4-(p-methoxybenzyloxy)-3-methyl-1-butenyl]-8-[(1R)-1-[(tert-butyldimethylsiloxy)methyl]-2-methylpropyl]-1-methylbicyclo[2.2.2]oct-5-en-2-ol

Downstream raw materials:

Toluene-4-sulfonic acid (R)-2-{(4'R,4'aS,8'R,8'aR)-4'-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-6'-methyl-3',4',4'a,7',8',8'a-hexahydro-1'H-spiro[[1,3]dioxolane-2,2'-naphthalen]-8'-yl}-3-methyl-butyl ester

Toluene-4-sulfonic acid (S)-2-{(4'R,4'aS,8'R,8'aR)-6'-methyl-8'-[(R)-2-methyl-1-(toluene-4-sulfonylmethyl)-propyl]-3',4',4'a,7',8',8'a-hexahydro-1'H-spiro[[1,3]dioxolane-2,2'-naphthalen]-4'-yl}-propyl ester

(4'R,4'aS,8'R,8'aR)-4'-[(S)-2-(4-Methoxy-benzyloxy)-1-methyl-ethyl]-6'-methyl-8'-[(R)-2-methyl-1-(toluene-4-sulfonylmethyl)-propyl]-3',4',4'a,7',8',8'a-hexahydro-1'H-spiro[[1,3]dioxolane-2,2'-naphthalene]

(4'R,4'aS,8'R,8'aR)-8'-((R)-1-Iodomethyl-2-methyl-propyl)-4'-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-6'-methyl-3',4',4'a,7',8',8'a-hexahydro-1'H-spiro[[1,3]dioxolane-2,2'-naphthalene]