Toluene-4-sulfonic acid (1S,5R)-7-oxo-bicyclo[3.2.0]hept-3-en-(6Z)-ylidenemethyl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid (1S,5R)-7-oxo-bicyclo[3.2.0]hept-3-en-(6Z)-ylidenemethyl ester
• CAS No.: 89849-79-6
• Molecular Formula: C₁₅H₁₄O₄S
• Molecular Weight: 290.34
• Mol file: 89849-79-6.mol

Synonyms:Toluene-4-sulfonic acid (1S,5R)-7-oxo-bicyclo[3.2.0]hept-3-en-(6Z)-ylidenemethyl ester

Chemical Property of Toluene-4-sulfonic acid (1S,5R)-7-oxo-bicyclo[3.2.0]hept-3-en-(6Z)-ylidenemethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Toluene-4-sulfonic acid (1S,5R)-7-oxo-bicyclo[3.2.0]hept-3-en-(6Z)-ylidenemethyl ester

There total 3 articles about Toluene-4-sulfonic acid (1S,5R)-7-oxo-bicyclo[3.2.0]hept-3-en-(6Z)-ylidenemethyl ester 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: 3.0%

p-toluenesulfonyl chloride (98-59-9) + (1R,5S)-7-[1-Hydroxy-meth-(Z)-ylidene]-bicyclo[3.2.0]hept-2-en-6-one → Toluene-4-sulfonic acid (1S,5R)-7-oxo-bicyclo[3.2.0]hept-3-en-(6E)-ylidenemethyl ester + Toluene-4-sulfonic acid (1S,5R)-7-oxo-bicyclo[3.2.0]hept-3-en-(6Z)-ylidenemethyl ester (89849-79-6)

Guidance literature:

at 0 ℃; for 0.75h;

DOI:10.1021/ja00321a063

Reference yield:

(1R,5S)-bicyclo[3.2.0]hept-2-en-6-one (71155-05-0) → Toluene-4-sulfonic acid (1S,5R)-7-oxo-bicyclo[3.2.0]hept-3-en-(6Z)-ylidenemethyl ester (89849-79-6)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydride / 1,2-dimethoxy-ethane / 3 h / 20 °C

2: 49 percent / 0.75 h / 0 °C

With sodium hydride; In 1,2-dimethoxyethane;

DOI:10.1021/ja00321a063

Reference yield:

tert-butyl formate (762-75-4) + (1R,5S)-bicyclo[3.2.0]hept-2-en-6-one (71155-05-0) + p-toluenesulfonyl chloride (98-59-9) → Toluene-4-sulfonic acid (1S,5R)-7-oxo-bicyclo[3.2.0]hept-3-en-(6E)-ylidenemethyl ester + Toluene-4-sulfonic acid (1S,5R)-7-oxo-bicyclo[3.2.0]hept-3-en-(6Z)-ylidenemethyl ester (89849-79-6)

Guidance literature:

With sodium hydride; Yield given. Multistep reaction; 1.) dimethoxyethane, 20 deg C, 3 h; 2.) 0 deg C, 45 min;

DOI:10.1021/ja00321a063

upstream raw materials:

tert-butyl formate

(1R,5S)-bicyclo[3.2.0]hept-2-en-6-one

p-toluenesulfonyl chloride