tert-Butyl-{5-(2-dimethoxymethyl-6-methoxy-benzyl)-2,4,4-trimethyl-3-[1-phenylsulfanyl-meth-(Z)-ylidene]-cyclohex-1-enyloxy}-dimethyl-silane

Base Information

• Chemical Name: tert-Butyl-{5-(2-dimethoxymethyl-6-methoxy-benzyl)-2,4,4-trimethyl-3-[1-phenylsulfanyl-meth-(Z)-ylidene]-cyclohex-1-enyloxy}-dimethyl-silane
• CAS No.: 122844-87-5
• Molecular Formula: C₃₃H₄₈O₄SSi
• Molecular Weight: 568.893
• Mol file: 122844-87-5.mol

Synonyms:

Chemical Property of tert-Butyl-{5-(2-dimethoxymethyl-6-methoxy-benzyl)-2,4,4-trimethyl-3-[1-phenylsulfanyl-meth-(Z)-ylidene]-cyclohex-1-enyloxy}-dimethyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-Butyl-{5-(2-dimethoxymethyl-6-methoxy-benzyl)-2,4,4-trimethyl-3-[1-phenylsulfanyl-meth-(Z)-ylidene]-cyclohex-1-enyloxy}-dimethyl-silane

There total 9 articles about tert-Butyl-{5-(2-dimethoxymethyl-6-methoxy-benzyl)-2,4,4-trimethyl-3-[1-phenylsulfanyl-meth-(Z)-ylidene]-cyclohex-1-enyloxy}-dimethyl-silane 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:

<(phenylthio)(trimethylsilyl)methyl>lithium (30536-77-7,167469-49-0) + 3-(tert-Butyl-dimethyl-silanyloxy)-5-(2-dimethoxymethyl-6-methoxy-benzyl)-2,6,6-trimethyl-cyclohex-2-enone (122844-86-4) → tert-Butyl-{5-(2-dimethoxymethyl-6-methoxy-benzyl)-2,4,4-trimethyl-3-[1-phenylsulfanyl-meth-(Z)-ylidene]-cyclohex-1-enyloxy}-dimethyl-silane (122844-87-5,122844-88-6)

Guidance literature:

With potassium tert-butylate; Multistep reaction;

DOI:10.1021/ja00203a039

Reference yield:

m-anisaldehyde dimethyl acetal (59276-28-7) → tert-Butyl-{5-(2-dimethoxymethyl-6-methoxy-benzyl)-2,4,4-trimethyl-3-[1-phenylsulfanyl-meth-(Z)-ylidene]-cyclohex-1-enyloxy}-dimethyl-silane (122844-87-5,122844-88-6)

Guidance literature:

Multi-step reaction with 7 steps

2: K₂CO₃ / methanol; H₂O / 7 h / Ambient temperature

3: PCC, NaOAc / CH₂Cl₂ / Ambient temperature

4: 1. LDA / 1. THF, -78 deg C, 1.5 h, 2. THF, a.) -78 deg C, 1.5 h, b.) 0 deg C, 1.5 h

5: t-BuOK / diethyl ether / 4 h / Ambient temperature

6: triethylamine / CH₂Cl₂ / 0.5 h / 0 °C

7: 1. BuLi / 1. THF, 0 deg C, 1 h; 2. THF a.) 0 deg C, 1 h, b.) r.t., 0.5 h

With n-butyllithium; potassium tert-butylate; sodium acetate; potassium carbonate; triethylamine; pyridinium chlorochromate; lithium diisopropyl amide; In methanol; diethyl ether; dichloromethane; water;

DOI:10.1016/S0040-4020(01)91209-8

Reference yield:

6-Bromo-4-hexen-3-yl acetate (122844-93-3) → tert-Butyl-{5-(2-dimethoxymethyl-6-methoxy-benzyl)-2,4,4-trimethyl-3-[1-phenylsulfanyl-meth-(Z)-ylidene]-cyclohex-1-enyloxy}-dimethyl-silane (122844-87-5,122844-88-6)

Guidance literature:

Multi-step reaction with 7 steps

2: K₂CO₃ / methanol; H₂O / 7 h / Ambient temperature

3: PCC, NaOAc / CH₂Cl₂ / Ambient temperature

4: 1. LDA / 1. THF, -78 deg C, 1.5 h, 2. THF, a.) -78 deg C, 1.5 h, b.) 0 deg C, 1.5 h

5: t-BuOK / diethyl ether / 4 h / Ambient temperature

6: triethylamine / CH₂Cl₂ / 0.5 h / 0 °C

7: 1. BuLi / 1. THF, 0 deg C, 1 h; 2. THF a.) 0 deg C, 1 h, b.) r.t., 0.5 h

With n-butyllithium; potassium tert-butylate; sodium acetate; potassium carbonate; triethylamine; pyridinium chlorochromate; lithium diisopropyl amide; In methanol; diethyl ether; dichloromethane; water;

DOI:10.1016/S0040-4020(01)91209-8

upstream raw materials:

(phenylsulfanylmethyl)trimethylsilane

3-(tert-Butyl-dimethyl-silanyloxy)-5-(2-dimethoxymethyl-6-methoxy-benzyl)-2,6,6-trimethyl-cyclohex-2-enone

<(phenylthio)(trimethylsilyl)methyl>lithium

m-anisaldehyde dimethyl acetal

Downstream raw materials:

(1S,9S,10S)-4,9-Dimethoxy-12,15,15-trimethyl-10-phenylsulfanyl-tricyclo[9.3.1.0^3,8]pentadeca-3⁽⁸⁾,4,6,11-tetraen-13-one