(2E,6S,7Z,10R,11R,12S,14RS)-6,10:14,15-diepoxy-11,12-(isopropylidenedioxy)-3,7,11,15-tetramethyl-1-(phenylthio)-2,7-hexadecadiene

Base Information

• Chemical Name: (2E,6S,7Z,10R,11R,12S,14RS)-6,10:14,15-diepoxy-11,12-(isopropylidenedioxy)-3,7,11,15-tetramethyl-1-(phenylthio)-2,7-hexadecadiene
• CAS No.: 195819-87-5
• Molecular Formula: C₂₉H₄₂O₄S
• Molecular Weight: 486.716
• Mol file: 195819-87-5.mol

Synonyms:(2E,6S,7Z,10R,11R,12S,14RS)-6,10:14,15-diepoxy-11,12-(isopropylidenedioxy)-3,7,11,15-tetramethyl-1-(phenylthio)-2,7-hexadecadiene

Chemical Property of (2E,6S,7Z,10R,11R,12S,14RS)-6,10:14,15-diepoxy-11,12-(isopropylidenedioxy)-3,7,11,15-tetramethyl-1-(phenylthio)-2,7-hexadecadiene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2E,6S,7Z,10R,11R,12S,14RS)-6,10:14,15-diepoxy-11,12-(isopropylidenedioxy)-3,7,11,15-tetramethyl-1-(phenylthio)-2,7-hexadecadiene

There total 29 articles about (2E,6S,7Z,10R,11R,12S,14RS)-6,10:14,15-diepoxy-11,12-(isopropylidenedioxy)-3,7,11,15-tetramethyl-1-(phenylthio)-2,7-hexadecadiene 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: 92.0%

thiophenol (108-98-5) + (2R,6S)-6-((E)-5-Bromo-3-methyl-pent-3-enyl)-2-[(4R,5S)-5-(3,3-dimethyl-oxiranylmethyl)-2,2,4-trimethyl-[1,3]dioxolan-4-yl]-5-methyl-3,6-dihydro-2H-pyran → (2E,6S,7Z,10R,11R,12S,14RS)-6,10:14,15-diepoxy-11,12-(isopropylidenedioxy)-3,7,11,15-tetramethyl-1-(phenylthio)-2,7-hexadecadiene (195819-87-5)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 0 - 25 ℃; for 1h;

DOI:10.1246/bcsj.71.1417

Reference yield:

(2E,6E)-3,7-dimethyl-8-oxoocta-2,6-dien-1-yl acetate (37905-02-5) → (2E,6S,7Z,10R,11R,12S,14RS)-6,10:14,15-diepoxy-11,12-(isopropylidenedioxy)-3,7,11,15-tetramethyl-1-(phenylthio)-2,7-hexadecadiene (195819-87-5)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 67 percent / NaOMe / methanol / 2 h / 25 °C

2.1: 97 percent / triethylamine / CH₂Cl₂ / 2 h / 0 - 25 °C

3.1: lithium bis(trimethylsilyl)amide / tetrahydrofuran / 0.25 h / -78 °C

3.2: 35 percent / tetrahydrofuran / 0.5 h / -78 °C

4.1: 47 percent / Zn(BH₄)2 / diethyl ether / 0.5 h / 0 °C

5.1: 58 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / benzene; H₂O / 24 h / 25 °C

6.1: 47 percent / d-10-camphorsulfonic acid / 2-methyl-propan-2-ol / 50 h / 25 °C

7.1: sodium bis(trimethylsilyl)amide / tetrahydrofuran / 0.67 h / -78 - 0 °C

7.2: 18 percent / tetrahydrofuran / 1 h / 0 - 20 °C

8.1: 74 percent / LiCl; PPh₃; Et₃SiH / [Pd(PPh₃)4] / dimethylformamide / 12 h / 60 °C

9.1: 50 percent / 3-chloroperbenzoic acid / CH₂Cl₂ / 4 h / -78 - 0 °C

10.1: 100 percent / LiAlH₄ / tetrahydrofuran / 4 h / -78 °C

11.1: 96 percent / 2,4,6-collidine; LiBr / CH₂Cl₂ / 1 h / 0 °C

12.1: 92 percent / NaH / dimethylformamide / 1 h / 0 - 25 °C

With 2,4,6-trimethyl-pyridine; triethylsilane; lithium aluminium tetrahydride; zinc(II) tetrahydroborate; camphor-10-sulfonic acid; sodium methylate; sodium hexamethyldisilazane; sodium hydride; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium chloride; lithium bromide; lithium hexamethyldisilazane; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; benzene; 1.1: Deacetylation / 2.1: Acylation / 3.1: Metallation / 3.2: Addition / 4.1: Reduction / 5.1: Oxidation / 6.1: Cyclization / 7.1: Metallation / 7.2: Esterification / 8.1: Reduction / 9.1: Epoxidation / 10.1: Reduction / 11.1: Substitution / 12.1: Substitution;

DOI:10.1246/bcsj.71.1417

Reference yield:

(2E,6E)-8-hydroxy-2,6-dimethylocta-2,6-dienal (38290-51-6) → (2E,6S,7Z,10R,11R,12S,14RS)-6,10:14,15-diepoxy-11,12-(isopropylidenedioxy)-3,7,11,15-tetramethyl-1-(phenylthio)-2,7-hexadecadiene (195819-87-5)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 97 percent / triethylamine / CH₂Cl₂ / 2 h / 0 - 25 °C

2.1: lithium bis(trimethylsilyl)amide / tetrahydrofuran / 0.25 h / -78 °C

2.2: 35 percent / tetrahydrofuran / 0.5 h / -78 °C

3.1: 47 percent / Zn(BH₄)2 / diethyl ether / 0.5 h / 0 °C

4.1: 58 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / benzene; H₂O / 24 h / 25 °C

5.1: 47 percent / d-10-camphorsulfonic acid / 2-methyl-propan-2-ol / 50 h / 25 °C

6.1: sodium bis(trimethylsilyl)amide / tetrahydrofuran / 0.67 h / -78 - 0 °C

6.2: 18 percent / tetrahydrofuran / 1 h / 0 - 20 °C

7.1: 74 percent / LiCl; PPh₃; Et₃SiH / [Pd(PPh₃)4] / dimethylformamide / 12 h / 60 °C

8.1: 50 percent / 3-chloroperbenzoic acid / CH₂Cl₂ / 4 h / -78 - 0 °C

9.1: 100 percent / LiAlH₄ / tetrahydrofuran / 4 h / -78 °C

10.1: 96 percent / 2,4,6-collidine; LiBr / CH₂Cl₂ / 1 h / 0 °C

11.1: 92 percent / NaH / dimethylformamide / 1 h / 0 - 25 °C

With 2,4,6-trimethyl-pyridine; triethylsilane; lithium aluminium tetrahydride; zinc(II) tetrahydroborate; camphor-10-sulfonic acid; sodium hexamethyldisilazane; sodium hydride; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium chloride; lithium bromide; lithium hexamethyldisilazane; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; benzene; 1.1: Acylation / 2.1: Metallation / 2.2: Addition / 3.1: Reduction / 4.1: Oxidation / 5.1: Cyclization / 6.1: Metallation / 6.2: Esterification / 7.1: Reduction / 8.1: Epoxidation / 9.1: Reduction / 10.1: Substitution / 11.1: Substitution;

DOI:10.1246/bcsj.71.1417

upstream raw materials:

sodium thiophenolate

thiophenol

Geraniol

(2E,6E)-3,7-dimethyl-8-oxoocta-2,6-dien-1-yl acetate

Downstream raw materials:

(1Z,3S,6E,8S,9R,11S,12R,13R)-3,13-epoxy-9-(1-hydroxy-1-methylethyl)-11,12-(isopropylidenedioxy)-2,6,12-trimethyl-8-(phenylthio)-1,6-cyclotetradecadiene

(1Z,3S,6E,8R,9S,11S,12R,13R)-3,13-epoxy-9-(1-hydroxy-1-methylethyl)-11,12-(isopropylidenedioxy)-2,6,12-trimethyl-8-(phenylthio)-1,6-cyclotetradecadiene