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

Base Information

• Chemical Name: Carbonic acid (1R,2S)-2-azido-1-(tert-butyl-diphenyl-silanyloxymethyl)-2-(4-methoxy-phenyl)-ethyl ester ethyl ester
• CAS No.: 237736-18-4
• Molecular Formula: C₂₉H₃₅N₃O₅Si
• Molecular Weight: 533.699
• Mol file: 237736-18-4.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 6 articles about Carbonic acid (1R,2S)-2-azido-1-(tert-butyl-diphenyl-silanyloxymethyl)-2-(4-methoxy-phenyl)-ethyl ester 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:

Carbonic acid (1R,2S)-3-(tert-butyl-diphenyl-silanyloxy)-2-ethoxycarbonyloxy-1-(4-methoxy-phenyl)-propyl ester ethyl ester → Carbonic acid (1R,2R)-2-azido-1-(tert-butyl-diphenyl-silanyloxymethyl)-2-(4-methoxy-phenyl)-ethyl ester ethyl ester + Carbonic acid (1R,2S)-2-azido-1-(tert-butyl-diphenyl-silanyloxymethyl)-2-(4-methoxy-phenyl)-ethyl ester ethyl ester (237736-18-4)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; trimethylsilylazide; In acetonitrile; at -43 ℃; Yield given; Yields of byproduct given;

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

Reference yield:

Carbonic acid (1S,2S)-3-(tert-butyl-diphenyl-silanyloxy)-2-ethoxycarbonyloxy-1-(4-methoxy-phenyl)-propyl ester ethyl ester (237736-17-3) → Carbonic acid (1R,2R)-2-azido-1-(tert-butyl-diphenyl-silanyloxymethyl)-2-(4-methoxy-phenyl)-ethyl ester ethyl ester + Carbonic acid (1R,2S)-2-azido-1-(tert-butyl-diphenyl-silanyloxymethyl)-2-(4-methoxy-phenyl)-ethyl ester ethyl ester (237736-18-4)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; trimethylsilylazide; In acetonitrile; at -43 ℃; Yield given; Yields of byproduct given;

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

Reference yield:

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate (24393-56-4) → Carbonic acid (1R,2S)-2-azido-1-(tert-butyl-diphenyl-silanyloxymethyl)-2-(4-methoxy-phenyl)-ethyl ester ethyl ester (237736-18-4)

Guidance literature:

Multi-step reaction with 5 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

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

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

upstream raw materials:

Carbonic acid (1S,2S)-3-(tert-butyl-diphenyl-silanyloxy)-2-ethoxycarbonyloxy-1-(4-methoxy-phenyl)-propyl 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:

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

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

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