[3-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-1-(4-methoxy-phenyl)-propyl]-carbamic acid tert-butyl ester

Base Information

• Chemical Name: [3-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-1-(4-methoxy-phenyl)-propyl]-carbamic acid tert-butyl ester
• CAS No.: 700359-87-1
• Molecular Formula: C₂₁H₃₇NO₅Si
• Molecular Weight: 411.614
• Mol file: 700359-87-1.mol

Synonyms:[3-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-1-(4-methoxy-phenyl)-propyl]-carbamic acid tert-butyl ester

Chemical Property of [3-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-1-(4-methoxy-phenyl)-propyl]-carbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [3-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-1-(4-methoxy-phenyl)-propyl]-carbamic acid tert-butyl ester

There total 11 articles about [3-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-1-(4-methoxy-phenyl)-propyl]-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: 92.0%

2R-amino-1-(tert-butyldimethylsiloxy)methyl-2-(4-methoxyphenyl)-(1R)-ethyl 4-nitrobenzoate (635313-43-8) → [3-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-1-(4-methoxy-phenyl)-propyl]-carbamic acid tert-butyl ester (700359-87-1)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; water; at 20 ℃; for 2h;

DOI:10.1081/SCC-120022181

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → [3-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-1-(4-methoxy-phenyl)-propyl]-carbamic acid tert-butyl ester (700359-87-1)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 6.6 g / Et₃N / tetrahydrofuran / 8 h / 20 °C

2.1: 99 percent / potassium carbonate / dimethylformamide / 7 h / 20 °C

3.1: 83.9 percent / NaBH₄; LiCl / ethanol; tetrahydrofuran / 16 h / 20 °C

4.1: oxalyl chloride; DMSO; N,N-diisopropylethyl amine / CH₂Cl₂ / -78 - 0 °C

5.1: 0.33 g / CH₂Cl₂; tetrahydrofuran / 20 °C

6.1: O₃ / CH₂Cl₂

6.2: 72.37 percent / NaBH₄ / methanol

7.1: 83 percent / imidazole / CH₂Cl₂ / 2 h

8.1: 63.5 percent / triphenyl phosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 24 h / 20 °C

9.1: 92 percent / LiOH / tetrahydrofuran; H₂O / 2 h / 20 °C

With 1H-imidazole; lithium hydroxide; sodium tetrahydroborate; oxalyl dichloride; di-isopropyl azodicarboxylate; potassium carbonate; ozone; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium chloride; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; 4.1: Swern oxidation / 5.1: Grignard reaction / 8.1: Mitsunobu reaction;

DOI:10.1081/SCC-120022181

Reference yield:

D-4-hydroxyphenylglycine (22818-40-2) → [3-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-1-(4-methoxy-phenyl)-propyl]-carbamic acid tert-butyl ester (700359-87-1)

Guidance literature:

Multi-step reaction with 10 steps

1.1: acetyl chloride / 3 h / Heating

2.1: 6.6 g / Et₃N / tetrahydrofuran / 8 h / 20 °C

3.1: 99 percent / potassium carbonate / dimethylformamide / 7 h / 20 °C

4.1: 83.9 percent / NaBH₄; LiCl / ethanol; tetrahydrofuran / 16 h / 20 °C

5.1: oxalyl chloride; DMSO; N,N-diisopropylethyl amine / CH₂Cl₂ / -78 - 0 °C

6.1: 0.33 g / CH₂Cl₂; tetrahydrofuran / 20 °C

7.1: O₃ / CH₂Cl₂

7.2: 72.37 percent / NaBH₄ / methanol

8.1: 83 percent / imidazole / CH₂Cl₂ / 2 h

9.1: 63.5 percent / triphenyl phosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 24 h / 20 °C

10.1: 92 percent / LiOH / tetrahydrofuran; H₂O / 2 h / 20 °C

With 1H-imidazole; lithium hydroxide; sodium tetrahydroborate; oxalyl dichloride; di-isopropyl azodicarboxylate; potassium carbonate; ozone; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; acetyl chloride; triphenylphosphine; lithium chloride; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; 5.1: Swern oxidation / 6.1: Grignard reaction / 9.1: Mitsunobu reaction;

DOI:10.1081/SCC-120022181

upstream raw materials:

2R-amino-1-(tert-butyldimethylsiloxy)methyl-2-(4-methoxyphenyl)-(1R)-ethyl 4-nitrobenzoate

di-tert-butyl dicarbonate

D-4-hydroxyphenylglycine

methyl (R)-2-amino-2-(4-hydroxyphenyl)acetate hydrochloride

Downstream raw materials:

(4R,5R)-cytoxazone

(2R,3R)-3-tert-butoxycarbonylamino-3-(4-methoxyphenyl)-1,2-propanediol