((Z)-(S)-3-Bromo-3-cyclohex-1-enyl-1-methyl-allyloxy)-tert-butyl-dimethyl-silane

Base Information

• Chemical Name: ((Z)-(S)-3-Bromo-3-cyclohex-1-enyl-1-methyl-allyloxy)-tert-butyl-dimethyl-silane
• CAS No.: 431874-77-0
• Molecular Formula: C₁₆H₂₉BrOSi
• Molecular Weight: 345.395
• Mol file: 431874-77-0.mol

Synonyms:((Z)-(S)-3-Bromo-3-cyclohex-1-enyl-1-methyl-allyloxy)-tert-butyl-dimethyl-silane

Chemical Property of ((Z)-(S)-3-Bromo-3-cyclohex-1-enyl-1-methyl-allyloxy)-tert-butyl-dimethyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((Z)-(S)-3-Bromo-3-cyclohex-1-enyl-1-methyl-allyloxy)-tert-butyl-dimethyl-silane

There total 3 articles about ((Z)-(S)-3-Bromo-3-cyclohex-1-enyl-1-methyl-allyloxy)-tert-butyl-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: 70.0%

1,1-dibromo-3(S)-<(tert-butyldimethylsilyl)oxy>-1-butene (163888-17-3) + cyclohex-1-enylboronic acid (89490-05-1,21190-87-4) → ((Z)-(S)-3-Bromo-3-cyclohex-1-enyl-1-methyl-allyloxy)-tert-butyl-dimethyl-silane (431874-77-0)

Guidance literature:

With barium dihydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; water; at 20 ℃; for 15h;

DOI:10.1021/ol0259746

Reference yield:

cyclohex-1-en-1-yl trifluoromethane sulfonate (28075-50-5) + 1,1-dibromo-3(S)-<(tert-butyldimethylsilyl)oxy>-1-butene (163888-17-3) → ((Z)-(S)-3-Bromo-3-cyclohex-1-enyl-1-methyl-allyloxy)-tert-butyl-dimethyl-silane (431874-77-0)

Guidance literature:

cyclohex-1-en-1-yl trifluoromethane sulfonate; With tetrakis(triphenylphosphine) palladium⁽⁰⁾; hexamethyldistannane; lithium chloride; In tetrahydrofuran; at 60 ℃;

1,1-dibromo-3(S)-<(tert-butyldimethylsilyl)oxy>-1-butene; With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; trifuran-2-yl-phosphane; In toluene; at 110 ℃; for 4h; Further stages.;

DOI:10.1021/ol025801g

Reference yield:

(S)-2-tert-butyl-dimethyl-silanyloxy propanal (87727-28-4) → ((Z)-(S)-3-Bromo-3-cyclohex-1-enyl-1-methyl-allyloxy)-tert-butyl-dimethyl-silane (431874-77-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 78 percent / PPh₃ / CH₂Cl₂ / -78 °C

2.1: (Me₃Sn)2; Pd(PPH₃)4; LiCl / tetrahydrofuran / 60 °C

2.2: Pd₂dba3; tris(2-furyl)phosphine / toluene / 4 h / 110 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; hexamethyldistannane; triphenylphosphine; lithium chloride; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ol025801g

upstream raw materials:

cyclohex-1-en-1-yl trifluoromethane sulfonate

1,1-dibromo-3(S)-<(tert-butyldimethylsilyl)oxy>-1-butene

cyclohex-1-enylboronic acid

(S)-2-tert-butyl-dimethyl-silanyloxy propanal

Downstream raw materials:

(Z)-(S)-4-Bromo-4-cyclohex-1-enyl-but-3-en-2-ol

Acrylic acid (Z)-(S)-3-bromo-3-cyclohex-1-enyl-1-methyl-allyl ester