4-allyl-5-(5-benzenesulfonyl-10-hydroxy-3,7,11-trimethyl-dodeca-2,6,11-trienyl)-2-(4-methoxy-benzyloxy)-5-methyl-cyclopent-2-enone

Base Information

• Chemical Name: 4-allyl-5-(5-benzenesulfonyl-10-hydroxy-3,7,11-trimethyl-dodeca-2,6,11-trienyl)-2-(4-methoxy-benzyloxy)-5-methyl-cyclopent-2-enone
• CAS No.: 935263-73-3
• Molecular Formula: C₃₈H₄₈O₆S
• Molecular Weight: 632.862
• Mol file: 935263-73-3.mol

Synonyms:4-allyl-5-(5-benzenesulfonyl-10-hydroxy-3,7,11-trimethyl-dodeca-2,6,11-trienyl)-2-(4-methoxy-benzyloxy)-5-methyl-cyclopent-2-enone

Chemical Property of 4-allyl-5-(5-benzenesulfonyl-10-hydroxy-3,7,11-trimethyl-dodeca-2,6,11-trienyl)-2-(4-methoxy-benzyloxy)-5-methyl-cyclopent-2-enone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-allyl-5-(5-benzenesulfonyl-10-hydroxy-3,7,11-trimethyl-dodeca-2,6,11-trienyl)-2-(4-methoxy-benzyloxy)-5-methyl-cyclopent-2-enone

There total 9 articles about 4-allyl-5-(5-benzenesulfonyl-10-hydroxy-3,7,11-trimethyl-dodeca-2,6,11-trienyl)-2-(4-methoxy-benzyloxy)-5-methyl-cyclopent-2-enone 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%

8-benzenesulfonyl-2,6-dimethyl-octa-1,6-dien-3-ol (935263-58-4) + 4-allyl-5-(4-bromo-3-methyl-but-2-enyl)-2-(4-methoxy-benzyloxy)-5-methyl-cyclopent-2-enone (935263-59-5) → 4-allyl-5-(5-benzenesulfonyl-10-hydroxy-3,7,11-trimethyl-dodeca-2,6,11-trienyl)-2-(4-methoxy-benzyloxy)-5-methyl-cyclopent-2-enone (935263-73-3)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium hexamethyldisilazane; In tetrahydrofuran; at -40 ℃; for 0.0833333h;

DOI:10.1021/ja070571s

Reference yield:

3,7-dimethyl-1-(phenylsulfonyl)-8-hydroxy-2(E),6(E)-octadiene (95763-61-4) → 4-allyl-5-(5-benzenesulfonyl-10-hydroxy-3,7,11-trimethyl-dodeca-2,6,11-trienyl)-2-(4-methoxy-benzyloxy)-5-methyl-cyclopent-2-enone (935263-73-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 80 percent / L-diethyl tartrate; TBHP / titanium tetraisopropoxide / CH₂Cl₂; decane / 20 h / -20 °C

2.1: pyridine; iodine; PPh₃ / acetonitrile; diethyl ether / 2 h / 0 °C

2.2: 74 percent / water / acetonitrile; diethyl ether / 8 h / 38 °C

3.1: 85 percent / LiHMDS; HMPA / tetrahydrofuran / 0.08 h / -40 °C

With pyridine; tert.-butylhydroperoxide; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl (2R,3R)-tartrate; iodine; triphenylphosphine; lithium hexamethyldisilazane; titanium(IV) isopropylate; In tetrahydrofuran; diethyl ether; decane; dichloromethane; acetonitrile; 1.1: Sharpless asymmetric epoxidation;

DOI:10.1021/ja070571s

Reference yield:

[3-(5-benzenesulfonyl-3-methyl-pent-3-enyl)-2-methyl-oxiranyl]-methanol (935263-72-2) → 4-allyl-5-(5-benzenesulfonyl-10-hydroxy-3,7,11-trimethyl-dodeca-2,6,11-trienyl)-2-(4-methoxy-benzyloxy)-5-methyl-cyclopent-2-enone (935263-73-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: pyridine; iodine; PPh₃ / acetonitrile; diethyl ether / 2 h / 0 °C

1.2: 74 percent / water / acetonitrile; diethyl ether / 8 h / 38 °C

2.1: 85 percent / LiHMDS; HMPA / tetrahydrofuran / 0.08 h / -40 °C

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; iodine; triphenylphosphine; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; acetonitrile;

DOI:10.1021/ja070571s

upstream raw materials:

8-benzenesulfonyl-2,6-dimethyl-octa-1,6-dien-3-ol

4-allyl-5-(4-bromo-3-methyl-but-2-enyl)-2-(4-methoxy-benzyloxy)-5-methyl-cyclopent-2-enone

[3-(5-benzenesulfonyl-3-methyl-pent-3-enyl)-2-methyl-oxiranyl]-methanol

5-methyl-5-(3-methyl-4-triisopropylsilanyloxy-but-2-enyl)-cyclopent-3-ene-1,2-dione

Downstream raw materials:

(?)-terpestacin

acetic acid 3-(2,3-dihydroxy-1-methyl-butyl)-2-(4-methoxy-benzyloxy)-6,10,14,16a-tetramethyl-1-oxo-1,3a,4,7,8,9,12,13,16,16a-decahydro-cyclopentacyclopentadecen-7-yl ester

acetic acid 3-(2-hydroxy-1-methyl-ethyl)-2-(4-methoxy-benzyloxy)-6,10,14,16a-tetramethyl-1-oxo-1,3a,4,7,8,9,12,13,16,16a-decahydro-cyclopentacyclopentadecen-7-yl ester

acetic acid 2-(4-methoxy-benzyloxy)-6,10,14,16a-tetramethyl-3-(1-methyl-but-2-enyl)-1-oxo-1,3a,4,7,8,9,12,13,16,16a-decahydro-cyclopentacyclopentadecen-7-yl ester