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

Base Information

• Chemical Name: (4S,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-4-(4-methoxy-phenyl)-oxazolidin-2-one
• CAS No.: 237736-20-8
• Molecular Formula: C₂₇H₃₁NO₄Si
• Molecular Weight: 461.633
• Mol file: 237736-20-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 8 articles about (4S,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-4-(4-methoxy-phenyl)-oxazolidin-2-one 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: 68.0%

[(1S,2R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-1-(4-methoxy-phenyl)-propyl]-carbamic acid ethyl ester (261381-17-3) → (4S,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-4-(4-methoxy-phenyl)-oxazolidin-2-one (237736-20-8)

Guidance literature:

With sodium hydride; In tetrahydrofuran; Ambient temperature;

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

Reference yield:

Carbonic acid (1R,2S)-2-azido-1-(tert-butyl-diphenyl-silanyloxymethyl)-2-(4-methoxy-phenyl)-ethyl ester phenyl ester (237736-25-3) → (4S,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-4-(4-methoxy-phenyl)-oxazolidin-2-one (237736-20-8)

Guidance literature:

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

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

Reference yield:

Ethyl threo-3-(p-methoxyphenyl)-2(R),3(S)-dihydroxypropionate (182268-43-5) → (4S,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-4-(4-methoxy-phenyl)-oxazolidin-2-one (237736-20-8)

Guidance literature:

Multi-step reaction with 6 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

6: 68 percent / NaH / tetrahydrofuran / Ambient temperature

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

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

upstream raw materials:

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

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

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

(1S,2S)-3-(tert-Butyl-diphenyl-silanyloxy)-1-(4-methoxy-phenyl)-propane-1,2-diol

Downstream raw materials:

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