(4aR,6R,8aS)-3,4,4a,5,6,7,8,8a-octahydro-8a-methyl-6-(phenylmethoxy)naphthalen-1-ol trifluoronethanesulfonate

Base Information

• Chemical Name: (4aR,6R,8aS)-3,4,4a,5,6,7,8,8a-octahydro-8a-methyl-6-(phenylmethoxy)naphthalen-1-ol trifluoronethanesulfonate
• CAS No.: 652153-15-6
• Molecular Formula: C₁₉H₂₃F₃O₄S
• Molecular Weight: 404.45
• Mol file: 652153-15-6.mol

Synonyms:(4aR,6R,8aS)-3,4,4a,5,6,7,8,8a-octahydro-8a-methyl-6-(phenylmethoxy)naphthalen-1-ol trifluoronethanesulfonate

Chemical Property of (4aR,6R,8aS)-3,4,4a,5,6,7,8,8a-octahydro-8a-methyl-6-(phenylmethoxy)naphthalen-1-ol trifluoronethanesulfonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4aR,6R,8aS)-3,4,4a,5,6,7,8,8a-octahydro-8a-methyl-6-(phenylmethoxy)naphthalen-1-ol trifluoronethanesulfonate

There total 1 articles about (4aR,6R,8aS)-3,4,4a,5,6,7,8,8a-octahydro-8a-methyl-6-(phenylmethoxy)naphthalen-1-ol trifluoronethanesulfonate 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: 90.0%

trifluoromethylsulfonic anhydride (358-23-6) + (4aR,6R,8aR)-6-Benzyloxy-8a-methyl-octahydro-naphthalen-1-one → (4aR,6R,8aS)-3,4,4a,5,6,7,8,8a-octahydro-8a-methyl-6-(phenylmethoxy)naphthalen-1-ol trifluoronethanesulfonate (652153-15-6)

Guidance literature:

With N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; In dichloromethane; at 20 ℃; for 16h;

DOI:10.1002/hlca.200390315

Reference yield: 83.0%

methanol (67-56-1) + carbon monoxide (201230-82-2) + (4aR,6R,8aS)-3,4,4a,5,6,7,8,8a-octahydro-8a-methyl-6-(phenylmethoxy)naphthalen-1-ol trifluoronethanesulfonate (652153-15-6) → (4aR,6R,8aS)-3,4,4a,5,6,7,8,8a-octahydro-8a-methyl-6-(phenylmethoxy)naphthalen-1-carboxylic acid methyl ester (652153-16-7)

Guidance literature:

With 1-methyl-pyrrolidin-2-one; potassium carbonate; lithium chloride; bis-triphenylphosphine-palladium(II) chloride; at 130 ℃; for 24h; under 10343 Torr;

DOI:10.1002/hlca.200390315

Reference yield:

(4aR,6R,8aS)-3,4,4a,5,6,7,8,8a-octahydro-8a-methyl-6-(phenylmethoxy)naphthalen-1-ol trifluoronethanesulfonate (652153-15-6) → (4aR,6R,8aS)-3,4,4a,5,6,7,8,8a-octahydro-8a-methyl-6-(phenylmethoxy)naphthalene-1-carboxaldehyde (652153-17-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 83 percent / K₂CO₃; LiCl; 1-methylpyrrolidin-2-one / dichlorobis(triphenylphosphine)palladium / 24 h / 130 °C / 10343 Torr

2: 86 percent / Dibal-H / CH₂Cl₂ / -78 °C

3: 89 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.75 h / 20 °C

With 1-methyl-pyrrolidin-2-one; diisobutylaluminium hydride; potassium carbonate; Dess-Martin periodane; lithium chloride; bis-triphenylphosphine-palladium(II) chloride; In dichloromethane;

DOI:10.1002/hlca.200390315

upstream raw materials:

trifluoromethylsulfonic anhydride

Downstream raw materials:

(4aR,6R,8aS)-3,4,4a,5,6,7,8,8a-octahydro-8a-methyl-6-(phenylmethoxy)naphthalen-1-carboxylic acid methyl ester

(4aR,6R,8aS)-3,4,4a,5,6,7,8,8a-octahydro-8a-methyl-6-(phenylmethoxy)naphthalene-1-carboxaldehyde

((4aR,6R,8aR)-6-Benzyloxy-8a-methyl-3,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl)-methanol

3-((4aR,6R,8aR)-6-Benzyloxy-8a-methyl-3,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl)-3-hydroxy-propionic acid tert-butyl ester