11S,12S-Bis-(p-toluensulfonyloxymethyl)-9,10-dihydro-9,10-ethano-anthracen

Base Information

• Chemical Name: 11S,12S-Bis-(p-toluensulfonyloxymethyl)-9,10-dihydro-9,10-ethano-anthracen
• CAS No.: 88929-24-2
• Molecular Formula: C₃₂H₃₀O₆S₂
• Molecular Weight: 574.719
• Mol file: 88929-24-2.mol

Synonyms:11S,12S-Bis-(p-toluensulfonyloxymethyl)-9,10-dihydro-9,10-ethano-anthracen

Chemical Property of 11S,12S-Bis-(p-toluensulfonyloxymethyl)-9,10-dihydro-9,10-ethano-anthracen

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 11S,12S-Bis-(p-toluensulfonyloxymethyl)-9,10-dihydro-9,10-ethano-anthracen

There total 8 articles about 11S,12S-Bis-(p-toluensulfonyloxymethyl)-9,10-dihydro-9,10-ethano-anthracen 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: 85.0%

(S,S)-11,12-bis(hydroxymethyl)-9,10-dihydro-9,10-ethanoanthracene (5445-55-6,26495-88-5,33216-02-3,41063-84-7,41204-44-8,71991-70-3) + p-toluenesulfonyl chloride (98-59-9) → 11S,12S-Bis-(p-toluensulfonyloxymethyl)-9,10-dihydro-9,10-ethano-anthracen (88929-24-2)

Guidance literature:

With pyridine; 1) 3 h, 0 deg C, 2) 15 h, -10 deg C;

Reference yield:

anthracene (120-12-7) → 11S,12S-Bis-(p-toluensulfonyloxymethyl)-9,10-dihydro-9,10-ethano-anthracen (88929-24-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 92 percent / dioxane / 80 h / Heating

2: 73 percent

3: 89 percent / LiAlH₄ / tetrahydrofuran / 1 h / Heating

4: 85 percent / pyridine / 1) 3 h, 0 deg C, 2) 15 h, -10 deg C

With pyridine; lithium aluminium tetrahydride; In tetrahydrofuran; 1,4-dioxane;

Reference yield:

trans-11,12-bis(hydroxymethyl)-9,10-dihydro-9,10-ethano-anthracene (5445-55-6,26495-88-5,33216-02-3,41063-84-7,41204-44-8,71991-70-3) → 11S,12S-Bis-(p-toluensulfonyloxymethyl)-9,10-dihydro-9,10-ethano-anthracen (88929-24-2)

Guidance literature:

Multi-step reaction with 2 steps

1: immobilized steapsin lipase / diethyl ether / 48 h / 20 °C / Enzymatic reaction

2: pyridine / 36 h / 0 °C / Inert atmosphere

With pyridine; immobilized steapsin lipase; In diethyl ether;

DOI:10.1016/j.tetasy.2011.06.016

upstream raw materials:

trans-11,12-bis(hydroxymethyl)-9,10-dihydro-9,10-ethano-anthracene

p-toluenesulfonyl chloride

racemic-9,10-dihydro-9,10-ethanoanthacene trans-dicarboxylic acid

(S,S)-11,12-bis(hydroxymethyl)-9,10-dihydro-9,10-ethanoanthracene

Downstream raw materials:

9,10-Aethano-anthracen