(1R,5S,7R)-1,4-dimethyl-2-oxa-7-p-toluenesulfonyloxybicyclo<3.2.2>nonan-3-one

Base Information

• Chemical Name: (1R,5S,7R)-1,4-dimethyl-2-oxa-7-p-toluenesulfonyloxybicyclo<3.2.2>nonan-3-one
• CAS No.: 157327-82-7
• Molecular Formula: C₁₇H₂₂O₅S
• Molecular Weight: 338.425
• Mol file: 157327-82-7.mol

Synonyms:(1R,5S,7R)-1,4-dimethyl-2-oxa-7-p-toluenesulfonyloxybicyclo<3.2.2>nonan-3-one

Chemical Property of (1R,5S,7R)-1,4-dimethyl-2-oxa-7-p-toluenesulfonyloxybicyclo<3.2.2>nonan-3-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,5S,7R)-1,4-dimethyl-2-oxa-7-p-toluenesulfonyloxybicyclo<3.2.2>nonan-3-one

There total 7 articles about (1R,5S,7R)-1,4-dimethyl-2-oxa-7-p-toluenesulfonyloxybicyclo<3.2.2>nonan-3-one 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: 92.0%

p-toluenesulfonyl chloride (98-59-9) + (1R,5S,7R)-1,4-dimethyl-7-hydroxy-2-oxabicyclo<3.2.2>nonan-3-one (157327-84-9) → (1R,5S,7R)-1,4-dimethyl-2-oxa-7-p-toluenesulfonyloxybicyclo<3.2.2>nonan-3-one (157327-82-7)

Guidance literature:

With dmap; In pyridine; for 67h; Ambient temperature;

DOI:10.1055/s-1994-25489

Reference yield:

(1R,5S,7R)-7-(1-ethoxyethoxy)-1-methyl-2-oxabicyclo<3.2.1>nonan-3-one (148679-94-1) → (1R,5S,7R)-1,4-dimethyl-2-oxa-7-p-toluenesulfonyloxybicyclo<3.2.2>nonan-3-one (157327-82-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 84 percent / lithium 1,1,1,3,3,3-hexamethyldisilazide / tetrahydrofuran; hexamethylphosphoric acid triamide / 16 h / Ambient temperature

2: pyridinium p-toluenesulfonate / methanol / 12 h / Ambient temperature

3: 92 percent / 4-(dimethylamino)pyridine / pyridine / 67 h / Ambient temperature

With dmap; pyridinium p-toluenesulfonate; lithium hexamethyldisilazane; In tetrahydrofuran; pyridine; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide;

DOI:10.1055/s-1994-25489

Reference yield:

(1R,5S,7R)-1,4-dimethyl-7-(1-ethoxyethoxy)-2-oxabicyclo<3.2.2>nonan-3-one → (1R,5S,7R)-1,4-dimethyl-2-oxa-7-p-toluenesulfonyloxybicyclo<3.2.2>nonan-3-one (157327-82-7)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridinium p-toluenesulfonate / methanol / 12 h / Ambient temperature

2: 92 percent / 4-(dimethylamino)pyridine / pyridine / 67 h / Ambient temperature

With dmap; pyridinium p-toluenesulfonate; In pyridine; methanol;

DOI:10.1055/s-1994-25489

upstream raw materials:

p-toluenesulfonyl chloride

(1R,5S,7R)-1,4-dimethyl-7-hydroxy-2-oxabicyclo<3.2.2>nonan-3-one

(1R,5S,7R)-7-(1-ethoxyethoxy)-1-methyl-2-oxabicyclo<3.2.1>nonan-3-one

1R,4S,6S-6-hydroxy-1-methylbicyclo<2.2.2>octan-2-one