(2E,6E,10E,14E)-3,7,11,15-tetramethyl-13-(phenylsulfonyl)[16,16,16-2H₃]hexadeca-2,6,10,14-tetraenoate

Base Information

• Chemical Name: (2E,6E,10E,14E)-3,7,11,15-tetramethyl-13-(phenylsulfonyl)[16,16,16-2H₃]hexadeca-2,6,10,14-tetraenoate
• CAS No.: 305838-25-9
• Molecular Formula: C₂₇H₃₈O₄S
• Molecular Weight: 461.638

Synonyms:(2E,6E,10E,14E)-3,7,11,15-tetramethyl-13-(phenylsulfonyl)[16,16,16-2H₃]hexadeca-2,6,10,14-tetraenoate

Chemical Property of (2E,6E,10E,14E)-3,7,11,15-tetramethyl-13-(phenylsulfonyl)[16,16,16-2H₃]hexadeca-2,6,10,14-tetraenoate

Chemical Property:

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Technology Process of (2E,6E,10E,14E)-3,7,11,15-tetramethyl-13-(phenylsulfonyl)[16,16,16-2H₃]hexadeca-2,6,10,14-tetraenoate

There total 6 articles about (2E,6E,10E,14E)-3,7,11,15-tetramethyl-13-(phenylsulfonyl)[16,16,16-2H₃]hexadeca-2,6,10,14-tetraenoate 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: 64.0%

methyl (2E,6E,10E,14E)-13-(methoxycarbonyl)-3,7,11,15-tetramethyl-13-(phenylsulfonyl)[16,16,16-2H3]hexadeca-2,6,10,14-tetraenoate (305838-24-8) → (2E,6E,10E,14E)-3,7,11,15-tetramethyl-13-(phenylsulfonyl)[16,16,16-2H3]hexadeca-2,6,10,14-tetraenoate (305838-25-9)

Guidance literature:

With 4-amino-phenol; caesium carbonate; In N,N-dimethyl-formamide; at 85 ℃; for 1.5h;

DOI:10.1002/1522-2675(20000809)83:8<2036::AID-HLCA2036>3.0.CO;2-5

Reference yield:

methyl (E,E)-farnesoate (3675-00-1) → (2E,6E,10E,14E)-3,7,11,15-tetramethyl-13-(phenylsulfonyl)[16,16,16-2H3]hexadeca-2,6,10,14-tetraenoate (305838-25-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: NaH / tetrahydrofuran / 20 °C

1.2: 34 percent / PdCl₂; CuCl₂; Ph₃P / tetrahydrofuran / 5 h / 20 °C

2.1: 64 percent / 4-aminophenol; Cs₂CO₃ / dimethylformamide / 1.5 h / 85 °C

With 4-amino-phenol; sodium hydride; caesium carbonate; In tetrahydrofuran; N,N-dimethyl-formamide; 1.1: deprotonation / 2.1: Decarboxylation;

DOI:10.1002/1522-2675(20000809)83:8<2036::AID-HLCA2036>3.0.CO;2-5

Reference yield:

(E)-[4,4,4-(2)H3]-3-methyl-2-butenyl bromide (125951-30-6) → (2E,6E,10E,14E)-3,7,11,15-tetramethyl-13-(phenylsulfonyl)[16,16,16-2H3]hexadeca-2,6,10,14-tetraenoate (305838-25-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 952 mg / dimethylformamide / 20 °C

2.1: BuLi / tetrahydrofuran; hexane / 0.17 h / -20 °C

2.2: 760 mg / tetrahydrofuran; hexane / 2 h / 20 °C

3.1: NaH / tetrahydrofuran / 20 °C

3.2: 34 percent / PdCl₂; CuCl₂; Ph₃P / tetrahydrofuran / 5 h / 20 °C

4.1: 64 percent / 4-aminophenol; Cs₂CO₃ / dimethylformamide / 1.5 h / 85 °C

With n-butyllithium; 4-amino-phenol; sodium hydride; caesium carbonate; In tetrahydrofuran; hexane; N,N-dimethyl-formamide; 1.1: Alkylation / 2.1: deprotonation / 3.1: deprotonation / 4.1: Decarboxylation;

DOI:10.1002/1522-2675(20000809)83:8<2036::AID-HLCA2036>3.0.CO;2-5

upstream raw materials:

methyl (2E,6E,10E,14E)-13-(methoxycarbonyl)-3,7,11,15-tetramethyl-13-(phenylsulfonyl)[16,16,16-2H₃]hexadeca-2,6,10,14-tetraenoate

methyl (E,E)-farnesoate

(E)-[4,4,4-⁽²⁾H₃]-3-methyl-2-butenyl bromide

(E)-[4,4,4-⁽²⁾H₃]-3-methyl-2-buten-1-ol

Downstream raw materials:

(2E,6E,10E,14E)-3,7,11,15-tetramethyl-13-(phenylsulfonyl)[16,16,16-2H₃]hexadeca-2,6,10,14-tetraen-1-ol

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