(1S,4R,7R,8R)-7,8-bis(benzyloxy)bicyclo[2.2.2]oct-5-en-2-one p-tosylhydrazone

Base Information

• Chemical Name: (1S,4R,7R,8R)-7,8-bis(benzyloxy)bicyclo[2.2.2]oct-5-en-2-one p-tosylhydrazone
• CAS No.: 652991-05-4
• Molecular Formula: C₂₉H₃₀N₂O₄S
• Molecular Weight: 502.634
• Mol file: 652991-05-4.mol

Synonyms:(1S,4R,7R,8R)-7,8-bis(benzyloxy)bicyclo[2.2.2]oct-5-en-2-one p-tosylhydrazone

Chemical Property of (1S,4R,7R,8R)-7,8-bis(benzyloxy)bicyclo[2.2.2]oct-5-en-2-one p-tosylhydrazone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,4R,7R,8R)-7,8-bis(benzyloxy)bicyclo[2.2.2]oct-5-en-2-one p-tosylhydrazone

There total 3 articles about (1S,4R,7R,8R)-7,8-bis(benzyloxy)bicyclo[2.2.2]oct-5-en-2-one p-tosylhydrazone 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: 94.0%

toluene-4-sulfonic acid hydrazide (1576-35-8) + (1S,4R,7R,8R)-7,8-bis(benzyloxy)bicyclo[2.2.2]oct-5-en-2-one (652991-03-2) → (1S,4R,7R,8R)-7,8-bis(benzyloxy)bicyclo[2.2.2]oct-5-en-2-one p-tosylhydrazone (652991-05-4)

Guidance literature:

In methanol; at 20 ℃; for 24h;

DOI:10.1039/b301271a

Reference yield:

(-)-(5R,6R)-5,6-bis(benzyloxy)cyclohexa-1,3-diene (514854-09-2) → (1S,4R,7R,8R)-7,8-bis(benzyloxy)bicyclo[2.2.2]oct-5-en-2-one p-tosylhydrazone (652991-05-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 69 percent / 2,6-lutidine / 12 h / 95 °C

2: 83 percent / aq. KOH / dimethylsulfoxide / 48 h / 20 °C

3: 94 percent / methanol / 24 h / 20 °C

With 2,6-dimethylpyridine; potassium hydroxide; In methanol; dimethyl sulfoxide; 1: Diels-Alder reaction;

DOI:10.1039/b301271a

Reference yield:

(1S,2R,4R,7R,8R)-7,8-Bis-benzyloxy-2-chloro-bicyclo[2.2.2]oct-5-ene-2-carbonitrile (652990-95-9) → (1S,4R,7R,8R)-7,8-bis(benzyloxy)bicyclo[2.2.2]oct-5-en-2-one p-tosylhydrazone (652991-05-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 83 percent / aq. KOH / dimethylsulfoxide / 48 h / 20 °C

2: 94 percent / methanol / 24 h / 20 °C

With potassium hydroxide; In methanol; dimethyl sulfoxide;

DOI:10.1039/b301271a

upstream raw materials:

toluene-4-sulfonic acid hydrazide

(1S,4R,7R,8R)-7,8-bis(benzyloxy)bicyclo[2.2.2]oct-5-en-2-one

(-)-(5R,6R)-5,6-bis(benzyloxy)cyclohexa-1,3-diene

(1S,2R,4R,7R,8R)-7,8-Bis-benzyloxy-2-chloro-bicyclo[2.2.2]oct-5-ene-2-carbonitrile

Downstream raw materials:

(7R,8R)-7,8-bis(benzyloxy)bicyclo[2.2.2]octa-2,5-diene