(1S,4R,5R,6R)-5-Benzenesulfonyl-6-phenylselanyl-7-oxa-bicyclo[2.2.1]heptan-2-one

Base Information

• Chemical Name: (1S,4R,5R,6R)-5-Benzenesulfonyl-6-phenylselanyl-7-oxa-bicyclo[2.2.1]heptan-2-one
• CAS No.: 105205-34-3
• Molecular Formula: C₁₈H₁₆O₄SSe
• Molecular Weight: 407.349
• Mol file: 105205-34-3.mol

Synonyms:(1S,4R,5R,6R)-5-Benzenesulfonyl-6-phenylselanyl-7-oxa-bicyclo[2.2.1]heptan-2-one

Chemical Property of (1S,4R,5R,6R)-5-Benzenesulfonyl-6-phenylselanyl-7-oxa-bicyclo[2.2.1]heptan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,4R,5R,6R)-5-Benzenesulfonyl-6-phenylselanyl-7-oxa-bicyclo[2.2.1]heptan-2-one

There total 1 articles about (1S,4R,5R,6R)-5-Benzenesulfonyl-6-phenylselanyl-7-oxa-bicyclo[2.2.1]heptan-2-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: 61.0%

phenylselenyl benzenesulfonate (60805-71-2) + 7-oxabicyclo[2.2.1]hept-5-en-2-one (95530-78-2) → (1S,4R,5R,6R)-5-Benzenesulfonyl-6-phenylselanyl-7-oxa-bicyclo[2.2.1]heptan-2-one (105205-34-3)

Guidance literature:

In benzene; at 20 ℃; for 3h; Irradiation;

DOI:10.1021/jo00376a054

Reference yield: 53.0%

(1S,4R,5R,6R)-5-Benzenesulfonyl-6-phenylselanyl-7-oxa-bicyclo[2.2.1]heptan-2-one (105205-34-3) → 5-benzenesulfonyl-7-oxabicyclo<2.2.1>hept-5-en-2-one (105183-37-7)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at -70 - -65 ℃; for 3h;

DOI:10.1021/jo00376a054

Reference yield:

(1S,4R,5R,6R)-5-Benzenesulfonyl-6-phenylselanyl-7-oxa-bicyclo[2.2.1]heptan-2-one (105205-34-3) → (1S,2R,7R,8S)-7-Benzenesulfonyl-6-methoxy-11-oxa-tricyclo[6.2.1.02,7]undecane-4,10-dione (115055-96-4,115115-56-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 53 percent / m-CPBA / CH₂Cl₂ / 3 h / -70 - -65 °C

2: 1.) hydroquinone, 2.) BF₃*Et₂O / 1.) toluene, 80 deg C, 2 h, 2.) toluene, 0 deg C, 30 min

With boron trifluoride diethyl etherate; hydroquinone; 3-chloro-benzenecarboperoxoic acid; In dichloromethane;

DOI:10.1021/jo00376a054

upstream raw materials:

phenylselenyl benzenesulfonate

7-oxabicyclo[2.2.1]hept-5-en-2-one

Downstream raw materials:

5-benzenesulfonyl-7-oxabicyclo<2.2.1>hept-5-en-2-one

(1RS,2SR,7RS,8RS)-7-benzenesulfonyl-11-oxatricyclo<6.2.1.0^2,7>undec-5-ene-4,10 dione

(1S,2R,7R,8S)-7-Benzenesulfonyl-6-methoxy-11-oxa-tricyclo[6.2.1.0^2,7]undecane-4,10-dione