(1R,2R)-1-Azido-3-(tert-butyl-diphenyl-silanyloxy)-1-(4-methoxy-phenyl)-propan-2-ol

Base Information

• Chemical Name: (1R,2R)-1-Azido-3-(tert-butyl-diphenyl-silanyloxy)-1-(4-methoxy-phenyl)-propan-2-ol
• CAS No.: 237736-14-0
• Molecular Formula: C₂₆H₃₁N₃O₃Si
• Molecular Weight: 461.636
• Mol file: 237736-14-0.mol

Synonyms:(1R,2R)-1-Azido-3-(tert-butyl-diphenyl-silanyloxy)-1-(4-methoxy-phenyl)-propan-2-ol

Chemical Property of (1R,2R)-1-Azido-3-(tert-butyl-diphenyl-silanyloxy)-1-(4-methoxy-phenyl)-propan-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2R)-1-Azido-3-(tert-butyl-diphenyl-silanyloxy)-1-(4-methoxy-phenyl)-propan-2-ol

There total 4 articles about (1R,2R)-1-Azido-3-(tert-butyl-diphenyl-silanyloxy)-1-(4-methoxy-phenyl)-propan-2-ol 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: 24.0%

tert-Butyl-[(4S,5S)-5-(4-methoxy-phenyl)-2-oxo-2λ4-[1,3,2]dioxathiolan-4-ylmethoxy]-diphenyl-silane (237736-13-9) → (2R,3R)-3-Azido-3-(4-methoxy-phenyl)-propane-1,2-diol (237736-22-0) + (1R,2R)-1-Azido-3-(tert-butyl-diphenyl-silanyloxy)-1-(4-methoxy-phenyl)-propan-2-ol (237736-14-0)

Guidance literature:

With lithium azide; In N,N-dimethyl-formamide; at 70 ℃;

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

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) + (2R,3R)-3-Azido-3-(4-methoxy-phenyl)-propane-1,2-diol (237736-22-0) → (1R,2R)-1-Azido-3-(tert-butyl-diphenyl-silanyloxy)-1-(4-methoxy-phenyl)-propan-2-ol (237736-14-0)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 0 ℃; 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) → (1R,2R)-1-Azido-3-(tert-butyl-diphenyl-silanyloxy)-1-(4-methoxy-phenyl)-propan-2-ol (237736-14-0)

Guidance literature:

Multi-step reaction with 5 steps

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

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

3: 99 percent / SOCl₂, Et₃N / CH₂Cl₂ / 0 °C

4: 24 percent / LiN₃ / dimethylformamide / 70 °C

5: imidazole / dimethylformamide / 0 °C

With 1H-imidazole; sodium tetrahydroborate; thionyl chloride; lithium azide; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

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

upstream raw materials:

tert-butylchlorodiphenylsilane

(2R,3R)-3-Azido-3-(4-methoxy-phenyl)-propane-1,2-diol

tert-Butyl-[(4S,5S)-5-(4-methoxy-phenyl)-2-oxo-2λ⁴-[1,3,2]dioxathiolan-4-ylmethoxy]-diphenyl-silane

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

Downstream raw materials:

(4R,5R)-5-(tert-butyldiphenylsilyloxymethyl)-4-(4-methoxyphenyl)oxazolidin-2-one

(4R,5R)-cytoxazone

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