Carbamic acid, [(1S,2S)-2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-5-hydroxy-1-phenylpent yl]-, 1,1-dimethylethyl ester

Base Information

• Chemical Name: Carbamic acid, [(1S,2S)-2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-5-hydroxy-1-phenylpent yl]-, 1,1-dimethylethyl ester
• CAS No.: 757195-54-3
• Molecular Formula: C22H39NO4Si
• Molecular Weight: 409.641
• Mol file: 757195-54-3.mol

Synonyms:

Chemical Property of Carbamic acid, [(1S,2S)-2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-5-hydroxy-1-phenylpent yl]-, 1,1-dimethylethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Carbamic acid, [(1S,2S)-2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-5-hydroxy-1-phenylpent yl]-, 1,1-dimethylethyl ester

There total 8 articles about Carbamic acid, [(1S,2S)-2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-5-hydroxy-1-phenylpent yl]-, 1,1-dimethylethyl 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: 74.5%

tert-butyl (1S,2S)-2-(tert-butyldimethylsilyloxy)-1-phenylpent-4-enylcarbamate (757195-53-2) → tert-butyl (1S,2S)-2-(tert-butyldimethylsilyloxy)-5-hydroxy-1-phenylpentylcarbamate (757195-54-3)

Guidance literature:

tert-butyl (1S,2S)-2-(tert-butyldimethylsilyloxy)-1-phenylpent-4-enylcarbamate; With diborane-dimethylsulfide complex; In tetrahydrofuran; at 20 ℃; for 4h;

With sodium hydroxide; dihydrogen peroxide; In tetrahydrofuran; at 20 ℃;

DOI:10.1021/ol0528235

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → tert-butyl (1S,2S)-2-(tert-butyldimethylsilyloxy)-5-hydroxy-1-phenylpentylcarbamate (757195-54-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 99 percent / Et₃N / CH₂Cl₂ / 38 h / 20 °C

2.1: DIBALH / CH₂Cl₂; toluene / 3.5 h / -78 °C

3.1: 379 mg / poly(4-(carboxymethylaminosulfonyl)styrene) with 2 percent DVB / acetonitrile / 20 °C

4.1: 89 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

5.1: B₂H₆*Me₂S / tetrahydrofuran / 4 h / 20 °C

5.2: 74.5 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran / 20 °C

With 2,6-dimethylpyridine; diborane-dimethylsulfide complex; poly(4-(carboxymethylaminosulfonyl)styrene) with 2 percent DVB; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; dichloromethane; toluene; acetonitrile;

DOI:10.1021/ol0528235

Reference yield:

(S)-2-phenylglycine (2935-35-5) → tert-butyl (1S,2S)-2-(tert-butyldimethylsilyloxy)-5-hydroxy-1-phenylpentylcarbamate (757195-54-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 78 percent / SOCl₂ / Heating

2.1: 99 percent / Et₃N / CH₂Cl₂ / 38 h / 20 °C

3.1: DIBALH / CH₂Cl₂; toluene / 3.5 h / -78 °C

4.1: 379 mg / poly(4-(carboxymethylaminosulfonyl)styrene) with 2 percent DVB / acetonitrile / 20 °C

5.1: 89 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

6.1: B₂H₆*Me₂S / tetrahydrofuran / 4 h / 20 °C

6.2: 74.5 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran / 20 °C

With 2,6-dimethylpyridine; thionyl chloride; diborane-dimethylsulfide complex; poly(4-(carboxymethylaminosulfonyl)styrene) with 2 percent DVB; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; dichloromethane; toluene; acetonitrile;

DOI:10.1021/ol0528235

upstream raw materials:

tert-butyl (1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-phenyl-4-pentenylcarbamate

tert-butyl (1S,2S)-2-(tert-butyldimethylsilyloxy)-1-phenylpent-4-enylcarbamate

di-tert-butyl dicarbonate

(S)-2-phenylglycine

Downstream raw materials:

(2S,3S)-tert-butyl 3-(tert-butyldimethylsilyloxy)-2-phenylpiperidine-1-carboxylate

tert-butyl (2S,3S)-3-hydroxy-2-phenylpiperidine-1-carboxylate