(Z)-(S)-8-(tert-Butyl-diphenyl-silanyloxy)-13-isopropenyl-6-methoxymethoxy-2,6-dimethyl-cyclotetradec-2-ene-4,9-diynone

Base Information

• Chemical Name: (Z)-(S)-8-(tert-Butyl-diphenyl-silanyloxy)-13-isopropenyl-6-methoxymethoxy-2,6-dimethyl-cyclotetradec-2-ene-4,9-diynone
• CAS No.: 190718-49-1
• Molecular Formula: C₃₇H₄₆O₄Si
• Molecular Weight: 582.855
• Mol file: 190718-49-1.mol

Synonyms:

Chemical Property of (Z)-(S)-8-(tert-Butyl-diphenyl-silanyloxy)-13-isopropenyl-6-methoxymethoxy-2,6-dimethyl-cyclotetradec-2-ene-4,9-diynone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-(S)-8-(tert-Butyl-diphenyl-silanyloxy)-13-isopropenyl-6-methoxymethoxy-2,6-dimethyl-cyclotetradec-2-ene-4,9-diynone

There total 15 articles about (Z)-(S)-8-(tert-Butyl-diphenyl-silanyloxy)-13-isopropenyl-6-methoxymethoxy-2,6-dimethyl-cyclotetradec-2-ene-4,9-diynone 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%

[(S)-9-(tert-Butyl-diphenyl-silanyloxy)-4-isopropenyl-11-methoxymethoxy-1,11-dimethyl-2,14-dioxo-tetradeca-7,12-diynyl]-phosphonic acid dimethyl ester (191214-02-5) → (Z)-(S)-8-(tert-Butyl-diphenyl-silanyloxy)-13-isopropenyl-6-methoxymethoxy-2,6-dimethyl-cyclotetradec-2-ene-4,9-diynone (190718-49-1)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride;

DOI:10.1021/jo970360d

Reference yield:

(-)-perillyl alcohol (536-59-4,18457-55-1) → (Z)-(S)-8-(tert-Butyl-diphenyl-silanyloxy)-13-isopropenyl-6-methoxymethoxy-2,6-dimethyl-cyclotetradec-2-ene-4,9-diynone (190718-49-1)

Guidance literature:

Multi-step reaction with 13 steps

1: 99 percent / VO(acac)2, t-BuOOH / CH₂Cl₂; decane / 0 - 20 °C

2: periodic acid / tetrahydrofuran; H₂O / 0 - 20 °C

3: p-TsOH

5: PPh₃

6: 1.) n-BuLi

7: imidazole / dimethylformamide

8: p-TsOH / H₂O

9: pyridinium dichromate

10: BuLi

11: 88 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / H₂O

12: 1.) oxalyl chloride, DMSO, 2.) triethylamine

13: 77 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene, LiCl

With 1H-imidazole; tert.-butylhydroperoxide; dipyridinium dichromate; n-butyllithium; oxalyl dichloride; bis(acetylacetonate)oxovanadium; toluene-4-sulfonic acid; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; periodic acid; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium chloride; In tetrahydrofuran; decane; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jo970360d

Reference yield:

((4S)-4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptan-1-yl)methanol (190718-78-6) → (Z)-(S)-8-(tert-Butyl-diphenyl-silanyloxy)-13-isopropenyl-6-methoxymethoxy-2,6-dimethyl-cyclotetradec-2-ene-4,9-diynone (190718-49-1)

Guidance literature:

Multi-step reaction with 12 steps

1: periodic acid / tetrahydrofuran; H₂O / 0 - 20 °C

2: p-TsOH

4: PPh₃

5: 1.) n-BuLi

6: imidazole / dimethylformamide

7: p-TsOH / H₂O

8: pyridinium dichromate

9: BuLi

10: 88 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / H₂O

11: 1.) oxalyl chloride, DMSO, 2.) triethylamine

12: 77 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene, LiCl

With 1H-imidazole; dipyridinium dichromate; n-butyllithium; oxalyl dichloride; toluene-4-sulfonic acid; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; periodic acid; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium chloride; In tetrahydrofuran; water; N,N-dimethyl-formamide;

DOI:10.1021/jo970360d

upstream raw materials:

[(S)-9-(tert-Butyl-diphenyl-silanyloxy)-4-isopropenyl-11-methoxymethoxy-1,11-dimethyl-2,14-dioxo-tetradeca-7,12-diynyl]-phosphonic acid dimethyl ester

(-)-perillyl alcohol

((4S)-4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptan-1-yl)methanol

(S)-5-formyl-4-isopropenylpentanoic acid

Downstream raw materials:

(Z)-(S)-8-(tert-Butyl-diphenyl-silanyloxy)-13-isopropenyl-6-methoxymethoxy-2,6-dimethyl-cyclotetradec-2-ene-4,9-diynol