(5S,6R)-6-methyl-5-(phenylsulfonylacetyl)bicyclo[2.2.1]hept-2-ene

Base Information

• Chemical Name: (5S,6R)-6-methyl-5-(phenylsulfonylacetyl)bicyclo[2.2.1]hept-2-ene
• CAS No.: 161713-91-3
• Molecular Formula: C₁₆H₁₈O₃S
• Molecular Weight: 290.383
• Mol file: 161713-91-3.mol

Synonyms:(5S,6R)-6-methyl-5-(phenylsulfonylacetyl)bicyclo[2.2.1]hept-2-ene

Chemical Property of (5S,6R)-6-methyl-5-(phenylsulfonylacetyl)bicyclo[2.2.1]hept-2-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5S,6R)-6-methyl-5-(phenylsulfonylacetyl)bicyclo[2.2.1]hept-2-ene

There total 2 articles about (5S,6R)-6-methyl-5-(phenylsulfonylacetyl)bicyclo[2.2.1]hept-2-ene 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: 89.0%

methylphenylsulfonate (3112-85-4) + 3-((1S,2S,3R,4R)-3-Methyl-bicyclo[2.2.1]hept-5-ene-2-carbonyl)-oxazolidin-2-one (109299-96-9) → (5S,6R)-6-methyl-5-(phenylsulfonylacetyl)bicyclo[2.2.1]hept-2-ene (161713-91-3)

Guidance literature:

methylphenylsulfonate; With n-butyllithium; In tetrahydrofuran; hexane; at 20 ℃; for 2h;

3-((1S,2S,3R,4R)-3-Methyl-bicyclo[2.2.1]hept-5-ene-2-carbonyl)-oxazolidin-2-one; In tetrahydrofuran; hexane; at 20 ℃; for 18h; optical yield given as %ee;

DOI:10.1055/s-0028-1083167

Reference yield:

(3E)-1-Phenylsulfonyl-2-oxo-3-pentene (96530-26-6) + cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) → (5S,6R)-6-methyl-5-(phenylsulfonylacetyl)bicyclo[2.2.1]hept-2-ene (161713-91-3) + (5R,6S)-6-methyl-5-(phenylsulfonylacetyl)bicyclo[2.2.1]hept-2-ene

Guidance literature:

(3E)-1-Phenylsulfonyl-2-oxo-3-pentene; With C₃₉H₄₄Br₂O₄Ti; In dichloromethane; at -78 ℃; for 0.5h; Molecular sieve; Inert atmosphere;

cyclopenta-1,3-diene; In dichloromethane; at -78 ℃; for 45h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1055/s-0028-1083167

upstream raw materials:

methylphenylsulfonate

3-((1S,2S,3R,4R)-3-Methyl-bicyclo[2.2.1]hept-5-ene-2-carbonyl)-oxazolidin-2-one

(3E)-1-Phenylsulfonyl-2-oxo-3-pentene

cyclopenta-1,3-diene