(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

Base Information

• Chemical Name: (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
• CAS No.: 211491-49-5
• Molecular Formula: C₂₉H₄₂O₄S
• Molecular Weight: 486.716
• Mol file: 211491-49-5.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 25 articles about (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 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: 77.0%

(2E,6S,7Z,10R,11R,12S,14S)-6,10:14,15-diepoxy-11,12-isopropylidenedioxy-3,7,11,15-tetramethyl-1-(phenylthio)hexadeca-2,7-diene (950598-33-1) → (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 (211491-49-5)

Guidance literature:

With n-butyllithium; dibutylmagnesium; In tetrahydrofuran; hexane; n-heptane; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1021/jo802249k

Reference yield: 54.0%

(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) → (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 (211491-49-5) + (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 (211491-51-9)

Guidance literature:

With n-butyllithium; dibutylmagnesium; In tetrahydrofuran; hexane; n-heptane; at 0 - 25 ℃; for 3h;

DOI:10.1246/bcsj.71.1417

Reference yield:

(2R,3R)-3-methyl-3-(4-methyl-3-pentenyl)oxiranemethanol (50727-94-1,62777-72-4,62960-04-7,71030-55-2,76985-26-7,82188-73-6,112456-40-3,112456-65-2,62777-71-3) → (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 (211491-49-5)

Guidance literature:

Multi-step reaction with 18 steps

1.1: 95 percent / triethylamine / dimethylformamide / 1 h / 0 - 25 °C

2.1: 2,6-lutidine / CH₂Cl₂ / 3 h / -78 °C

4.1: 50 percent / titanium(IV) isopropoxide / tetrahydrofuran / 21 h / 25 °C

5.1: 96 percent / DMSO; oxalyl dichloride; triethylamine / CH₂Cl₂ / 1 h / -78 - 0 °C

6.1: 95 percent / NaOMe / methanol / 2 h / 25 °C

7.1: 90 percent / d-10-camphorsulfonic acid / CH₂Cl₂ / 1.5 h / 25 °C

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

8.2: 35 percent / tetrahydrofuran / 0.5 h / -78 °C

9.1: 47 percent / Zn(BH₄)2 / diethyl ether / 0.5 h / 0 °C

10.1: 58 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / benzene; H₂O / 24 h / 25 °C

11.1: 47 percent / d-10-camphorsulfonic acid / 2-methyl-propan-2-ol / 50 h / 25 °C

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

12.2: 18 percent / tetrahydrofuran / 1 h / 0 - 20 °C

13.1: 74 percent / LiCl; PPh₃; Et₃SiH / [Pd(PPh₃)4] / dimethylformamide / 12 h / 60 °C

14.1: 50 percent / 3-chloroperbenzoic acid / CH₂Cl₂ / 4 h / -78 - 0 °C

15.1: 100 percent / LiAlH₄ / tetrahydrofuran / 4 h / -78 °C

16.1: 96 percent / 2,4,6-collidine; LiBr / CH₂Cl₂ / 1 h / 0 °C

17.1: 92 percent / NaH / dimethylformamide / 1 h / 0 - 25 °C

18.1: 54 percent / Bu₂Mg; n-BuLi / heptane; hexane; tetrahydrofuran / 3 h / 0 - 25 °C

With 2,6-dimethylpyridine; 2,4,6-trimethyl-pyridine; titanium(IV) isopropylate; triethylsilane; lithium aluminium tetrahydride; n-butyllithium; zinc(II) tetrahydroborate; oxalyl dichloride; camphor-10-sulfonic acid; dibutylmagnesium; sodium methylate; sodium hexamethyldisilazane; sodium hydride; dimethyl sulfoxide; 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; hexane; n-heptane; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; benzene; 1.1: silylation / 2.1: Ring cleavage / 4.1: Ring cleavage / 5.1: Swern oxidation / 6.1: Deacetylation / 7.1: Cyclization / 8.1: Metallation / 8.2: Addition / 9.1: Reduction / 10.1: Oxidation / 11.1: Cyclization / 12.1: Metallation / 12.2: Esterification / 13.1: Reduction / 14.1: Epoxidation / 15.1: Reduction / 16.1: Substitution / 17.1: Substitution / 18.1: Ito-Kodama cyclization;

DOI:10.1246/bcsj.71.1417

upstream raw materials:

(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

Geraniol

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

(2E,6E)-8-hydroxy-2,6-dimethylocta-2,6-dienal