trans-3-<2'-bromo-3'-(2''-bromoethyl)-6'-methoxyphenoxy>-4-<(tert-butyldimethylsilyl)oxy>-1-(phenylsulfonyl)-2-(2'''-propenyl)cyclohexene

Base Information

• Chemical Name: trans-3-<2'-bromo-3'-(2''-bromoethyl)-6'-methoxyphenoxy>-4-<(tert-butyldimethylsilyl)oxy>-1-(phenylsulfonyl)-2-(2'''-propenyl)cyclohexene
• CAS No.: 105728-98-1
• Molecular Formula: C₃₀H₄₀Br₂O₅SSi
• Molecular Weight: 700.604
• Mol file: 105728-98-1.mol

Synonyms:trans-3-<2'-bromo-3'-(2''-bromoethyl)-6'-methoxyphenoxy>-4-<(tert-butyldimethylsilyl)oxy>-1-(phenylsulfonyl)-2-(2'''-propenyl)cyclohexene

Chemical Property of trans-3-<2'-bromo-3'-(2''-bromoethyl)-6'-methoxyphenoxy>-4-<(tert-butyldimethylsilyl)oxy>-1-(phenylsulfonyl)-2-(2'''-propenyl)cyclohexene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of trans-3-<2'-bromo-3'-(2''-bromoethyl)-6'-methoxyphenoxy>-4-<(tert-butyldimethylsilyl)oxy>-1-(phenylsulfonyl)-2-(2'''-propenyl)cyclohexene

There total 10 articles about trans-3-<2'-bromo-3'-(2''-bromoethyl)-6'-methoxyphenoxy>-4-<(tert-butyldimethylsilyl)oxy>-1-(phenylsulfonyl)-2-(2'''-propenyl)cyclohexene 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: 85.0%

2-bromo-3-(2'-bromoethyl)-6-methoxyphenol (105728-94-7) + cis-4-<(tert-butyldimethylsilyl)oxy>-3-hydroxy-1-(phenylsulfonyl)-2-(2'-propenyl)cyclohexene (105728-97-0) → trans-3-<2'-bromo-3'-(2''-bromoethyl)-6'-methoxyphenoxy>-4-<(tert-butyldimethylsilyl)oxy>-1-(phenylsulfonyl)-2-(2'''-propenyl)cyclohexene (105728-98-1)

Guidance literature:

With tributylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 25 ℃; for 0.5h;

DOI:10.1021/jo00379a038

Reference yield: 80.0%

cis-4-<(tert-butyldimethylsilyl)oxy>-3-hydroxy-1-(phenylsulfonyl)-2-(2'-propenyl)cyclohexene (105728-97-0) → trans-3-<2'-bromo-3'-(2''-bromoethyl)-6'-methoxyphenoxy>-4-<(tert-butyldimethylsilyl)oxy>-1-(phenylsulfonyl)-2-(2'''-propenyl)cyclohexene (105728-98-1)

Guidance literature:

With tributylphosphine; diethylazodicarboxylate; In tetrahydrofuran; for 0.75h; Ambient temperature;

DOI:10.1021/jo00255a008

Reference yield:

isovanillin (621-59-0) → trans-3-<2'-bromo-3'-(2''-bromoethyl)-6'-methoxyphenoxy>-4-<(tert-butyldimethylsilyl)oxy>-1-(phenylsulfonyl)-2-(2'''-propenyl)cyclohexene (105728-98-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 70 percent / Br₂, NaOAc, HOAc / 2 h / 25 °C

2: 80 percent / NaH / dimethylformamide / 18 h / 25 °C

3: 86 percent / 5 N NaOH / benzene / 12 h / 25 °C

4: 1.) (Sia)2BH, 2.) H₂O₂, NaOH / 1.) THF, 0 deg C, 1 h, 2.) THF, 0 deg C, 1 h

5: 93 percent / TsOH / methanol / 4 h / 25 °C

6: 92 percent / CBr₄, (C₆H₅)3P / acetonitrile / 1 h / 25 °C

7: 85 percent / n-Bu₃P, diethyl azodicarboxylate (DEAD) / tetrahydrofuran / 0.5 h / 25 °C

With sodium hydroxide; carbon tetrabromide; tributylphosphine; (Sia)2BH; dihydrogen peroxide; bromine; sodium acetate; sodium hydride; toluene-4-sulfonic acid; acetic acid; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; acetonitrile; benzene;

DOI:10.1021/jo00379a038

upstream raw materials:

2-bromo-3-(2'-bromoethyl)-6-methoxyphenol

cis-4-<(tert-butyldimethylsilyl)oxy>-3-hydroxy-1-(phenylsulfonyl)-2-(2'-propenyl)cyclohexene

isovanillin

2-bromoisovanillin

Downstream raw materials:

trans-3-<2'-bromo-3'-(2''-bromoethyl)-6'-methoxyphenoxy>-4-hydroxy-1-(phenylsulfonyl)-2-(2'''-propenyl)cyclohexene

(dl)-1,2,3,3a(R),8,9,9a,9b-octahydro-3(S)-hydroxy-5-methoxy-9a(R)-(phenylsulfonyl)-9b(S)-(2'-propenyl)phenanthro<4,4a,4b,5-bcd>-furan

cis-2-(3'-(2''-bromoethyl)-6'-methoxyphenoxy)-1-hydroxy-3-(2'''-propen-1'''-ylidene)-4-(phenylsulfonyl)cyclohexane

2-<2'-bromo-3'-(2''-bromoethyl)-6'-methoxyphenoxy>-4-(phenylsulfonyl)-3-(2'''-propenyl)cyclohex-3-enone