[(1R,2R)-2-(2-Benzyloxy-5-bromo-phenoxy)-1-methoxymethoxymethyl-2-methyl-butyl]-carbamic acid tert-butyl ester

Base Information

• Chemical Name: [(1R,2R)-2-(2-Benzyloxy-5-bromo-phenoxy)-1-methoxymethoxymethyl-2-methyl-butyl]-carbamic acid tert-butyl ester
• CAS No.: 401606-61-9
• Molecular Formula: C₂₆H₃₆BrNO₆
• Molecular Weight: 538.479

Synonyms:[(1R,2R)-2-(2-Benzyloxy-5-bromo-phenoxy)-1-methoxymethoxymethyl-2-methyl-butyl]-carbamic acid tert-butyl ester

Chemical Property of [(1R,2R)-2-(2-Benzyloxy-5-bromo-phenoxy)-1-methoxymethoxymethyl-2-methyl-butyl]-carbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(1R,2R)-2-(2-Benzyloxy-5-bromo-phenoxy)-1-methoxymethoxymethyl-2-methyl-butyl]-carbamic acid tert-butyl ester

There total 9 articles about [(1R,2R)-2-(2-Benzyloxy-5-bromo-phenoxy)-1-methoxymethoxymethyl-2-methyl-butyl]-carbamic acid tert-butyl ester 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: 96.0%

benzyl bromide (100-39-0) + [(1R,2R)-2-(5-Bromo-2-hydroxy-phenoxy)-1-methoxymethoxymethyl-2-methyl-butyl]-carbamic acid tert-butyl ester (401606-60-8) → [(1R,2R)-2-(2-Benzyloxy-5-bromo-phenoxy)-1-methoxymethoxymethyl-2-methyl-butyl]-carbamic acid tert-butyl ester (401606-61-9)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; potassium carbonate; In N,N-dimethyl-formamide; for 18h;

DOI:10.1021/ja017277z

Reference yield:

(2R,3R) 2-<(tert-butoxycarbonyl)amino>-3-methyl-1,3-pentanediol (167102-72-9) → [(1R,2R)-2-(2-Benzyloxy-5-bromo-phenoxy)-1-methoxymethoxymethyl-2-methyl-butyl]-carbamic acid tert-butyl ester (401606-61-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 3.09 g / iPr₂NEt / CH₂Cl₂ / 14 h / 25 °C

2: 78 percent / TFA / CH₂Cl₂ / 0.83 h / 0 °C

3: 78.2 percent / KHMDS / tetrahydrofuran; toluene / 2 h / 0 °C

4: 81 percent / Et₃N / CH₂Cl₂ / 0 - 20 °C

5: 56 percent / NaH₂PO₂; pyridine; AcOH / Raney nickel / H₂O / 4.33 h / 0 - 47 °C

6: 2.49 g / aq. H₂O₂; bis(2-nitrophenyl)diselenide / CH₂Cl₂ / 24 h / 20 °C

7: 73 percent / methanilic KOH / 1.5 h / 20 °C

8: 96 percent / K₂CO₃; n-Bu₄NI / dimethylformamide / 18 h

With pyridine; potassium hydroxide; sodium hypophosphite; bis(o-nitrophenyl) diselenide; dihydrogen peroxide; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; potassium carbonate; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; nickel; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; toluene; 6: Dakin oxidation;

DOI:10.1021/ja017277z

Reference yield:

(R)-4-((R)-1-hydroxy-1-methylpropyl)-2,2-dimethyl oxazolidine-3-carboxylic acid tert-butyl ester (167102-68-3) → [(1R,2R)-2-(2-Benzyloxy-5-bromo-phenoxy)-1-methoxymethoxymethyl-2-methyl-butyl]-carbamic acid tert-butyl ester (401606-61-9)

Guidance literature:

Multi-step reaction with 9 steps

1: p-TsOH / methanol / 0.5 h / 20 °C

2: 3.09 g / iPr₂NEt / CH₂Cl₂ / 14 h / 25 °C

3: 78 percent / TFA / CH₂Cl₂ / 0.83 h / 0 °C

4: 78.2 percent / KHMDS / tetrahydrofuran; toluene / 2 h / 0 °C

5: 81 percent / Et₃N / CH₂Cl₂ / 0 - 20 °C

6: 56 percent / NaH₂PO₂; pyridine; AcOH / Raney nickel / H₂O / 4.33 h / 0 - 47 °C

7: 2.49 g / aq. H₂O₂; bis(2-nitrophenyl)diselenide / CH₂Cl₂ / 24 h / 20 °C

8: 73 percent / methanilic KOH / 1.5 h / 20 °C

9: 96 percent / K₂CO₃; n-Bu₄NI / dimethylformamide / 18 h

With pyridine; potassium hydroxide; sodium hypophosphite; bis(o-nitrophenyl) diselenide; dihydrogen peroxide; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; potassium carbonate; toluene-4-sulfonic acid; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; nickel; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; 7: Dakin oxidation;

DOI:10.1021/ja017277z

upstream raw materials:

benzyl bromide

[(1R,2R)-2-(5-Bromo-2-hydroxy-phenoxy)-1-methoxymethoxymethyl-2-methyl-butyl]-carbamic acid tert-butyl ester

(2R,3R) 2-<(tert-butoxycarbonyl)amino>-3-methyl-1,3-pentanediol

(R)-4-((R)-1-hydroxy-1-methylpropyl)-2,2-dimethyl oxazolidine-3-carboxylic acid tert-butyl ester

Downstream raw materials:

(E)-3-[4-Benzyloxy-3-((1R,2R)-2-tert-butoxycarbonylamino-1-ethyl-3-methoxymethoxy-1-methyl-propoxy)-phenyl]-acrylic acid ethyl ester

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