[(1S,2R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-1-(4-methoxy-phenyl)-propyl]-carbamic acid ethyl ester

Base Information

• Chemical Name: [(1S,2R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-1-(4-methoxy-phenyl)-propyl]-carbamic acid ethyl ester
• CAS No.: 261381-17-3
• Molecular Formula: C₂₉H₃₇NO₅Si
• Molecular Weight: 507.702
• Mol file: 261381-17-3.mol

Synonyms:[(1S,2R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-1-(4-methoxy-phenyl)-propyl]-carbamic acid ethyl ester

Chemical Property of [(1S,2R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-1-(4-methoxy-phenyl)-propyl]-carbamic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(1S,2R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-1-(4-methoxy-phenyl)-propyl]-carbamic acid ethyl ester

There total 7 articles about [(1S,2R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-1-(4-methoxy-phenyl)-propyl]-carbamic acid ethyl 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: 53.0%

Carbonic acid (1R,2S)-2-azido-1-(tert-butyl-diphenyl-silanyloxymethyl)-2-(4-methoxy-phenyl)-ethyl ester ethyl ester (237736-18-4) → [(1S,2R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-1-(4-methoxy-phenyl)-propyl]-carbamic acid ethyl ester (261381-17-3)

Guidance literature:

With triphenylphosphine; In tetrahydrofuran; water; at 50 ℃;

DOI:10.1016/S0040-4039(99)00712-1

Reference yield:

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate (24393-56-4) → [(1S,2R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-1-(4-methoxy-phenyl)-propyl]-carbamic acid ethyl ester (261381-17-3)

Guidance literature:

Multi-step reaction with 6 steps

1: AD-mix-α / 2-methyl-propan-2-ol; H2O / Ambient temperature

2: 66 percent / NaBH₄ / tetrahydrofuran / 0 °C

3: 99 percent / imidazole / dimethylformamide / 0 °C

4: 92 percent / pyridine / CH₂Cl₂ / 0 °C

5: TMSN₃, TMSOTf / acetonitrile / -43 °C

6: 53 percent / PPh₃ / tetrahydrofuran; H₂O / 50 °C

With pyridine; 1H-imidazole; sodium tetrahydroborate; AD-mix-α; trimethylsilyl trifluoromethanesulfonate; trimethylsilylazide; triphenylphosphine; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol;

DOI:10.1016/S0040-4039(99)00712-1

Reference yield:

Ethyl threo-3-(p-methoxyphenyl)-2(R),3(S)-dihydroxypropionate (182268-43-5) → [(1S,2R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-1-(4-methoxy-phenyl)-propyl]-carbamic acid ethyl ester (261381-17-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 66 percent / NaBH₄ / tetrahydrofuran / 0 °C

2: 99 percent / imidazole / dimethylformamide / 0 °C

3: 92 percent / pyridine / CH₂Cl₂ / 0 °C

4: TMSN₃, TMSOTf / acetonitrile / -43 °C

5: 53 percent / PPh₃ / tetrahydrofuran; H₂O / 50 °C

With pyridine; 1H-imidazole; sodium tetrahydroborate; trimethylsilyl trifluoromethanesulfonate; trimethylsilylazide; triphenylphosphine; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0040-4039(99)00712-1

upstream raw materials:

Carbonic acid (1R,2S)-2-azido-1-(tert-butyl-diphenyl-silanyloxymethyl)-2-(4-methoxy-phenyl)-ethyl ester ethyl ester

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate

Ethyl threo-3-(p-methoxyphenyl)-2(R),3(S)-dihydroxypropionate

(1S,2S)-1-(4-Methoxy-phenyl)-propane-1,2,3-triol

Downstream raw materials:

(4S,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-4-(4-methoxy-phenyl)-oxazolidin-2-one

(-)-(4S,5R)-5-hydroxymethyl-4-(4-methoxyphenyl)-1,3-oxazolidin-2-one