(2R,3R)-3-azido-1-(tert-butyldimethylsilyloxy)-3-(4-methoxyphenyl)-2-propanol

Base Information

• Chemical Name: (2R,3R)-3-azido-1-(tert-butyldimethylsilyloxy)-3-(4-methoxyphenyl)-2-propanol
• CAS No.: 254761-49-4
• Molecular Formula: C₁₆H₂₇N₃O₃Si
• Molecular Weight: 337.494
• Mol file: 254761-49-4.mol

Synonyms:(2R,3R)-3-azido-1-(tert-butyldimethylsilyloxy)-3-(4-methoxyphenyl)-2-propanol

Chemical Property of (2R,3R)-3-azido-1-(tert-butyldimethylsilyloxy)-3-(4-methoxyphenyl)-2-propanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R)-3-azido-1-(tert-butyldimethylsilyloxy)-3-(4-methoxyphenyl)-2-propanol

There total 1 articles about (2R,3R)-3-azido-1-(tert-butyldimethylsilyloxy)-3-(4-methoxyphenyl)-2-propanol 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: 61.0%

(4S,5S)-5-(tert-butyldimethylsilyloxymethyl)-4-(4-methoxyphenyl)-1,3,2-dioxathiolane 2-oxide → (2S,3S)-2-azido-1-(tert-butyldimethylsilyloxy)-3-(4-methoxyphenyl)-3-propanol + (2R,3R)-3-azido-1-(tert-butyldimethylsilyloxy)-3-(4-methoxyphenyl)-2-propanol (254761-49-4)

Guidance literature:

With lithium azide; In N,N-dimethyl-formamide; at 100 ℃; for 2h;

DOI:10.1002/(sici)1099-0690(199911)1999:11<2965::aid-ejoc2965>3.0.co;2-h

Reference yield: 87.0%

(2R,3R)-3-azido-1-(tert-butyldimethylsilyloxy)-3-(4-methoxyphenyl)-2-propanol (254761-49-4) → (2R,3R)-3-amino-1-(tert-butyldimethylsilyloxy)-3-(4-methoxyphenyl)-2-propanol (254761-50-7)

Guidance literature:

With ammonium formate; palladium on activated charcoal; In methanol; at 50 ℃; for 4h;

DOI:10.1002/(sici)1099-0690(199911)1999:11<2965::aid-ejoc2965>3.0.co;2-h

Reference yield:

(2R,3R)-3-azido-1-(tert-butyldimethylsilyloxy)-3-(4-methoxyphenyl)-2-propanol (254761-49-4) → (4R,5R)-cytoxazone (220736-25-4,259794-13-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 87 percent / ammonium formate / Pd/C / methanol / 4 h / 50 °C

2: 66 percent / K₂CO₃ / 2 h / 120 °C

3: 89 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.17 h / 20 °C

With tetrabutyl ammonium fluoride; ammonium formate; potassium carbonate; palladium on activated charcoal; In tetrahydrofuran; methanol; 1: Reduction / 2: cyclocondensation / 3: desilylation;

DOI:10.1002/(sici)1099-0690(199911)1999:11<2965::aid-ejoc2965>3.0.co;2-h

Downstream raw materials:

(2R,3R)-3-amino-1-(tert-butyldimethylsilyloxy)-3-(4-methoxyphenyl)-2-propanol

(4R,5R)-cytoxazone

(4R,5R)-5-(((tert-butyldimethylsilyl)oxy)methyl)-4-(4-methoxyphenyl)oxazolidin-2-one