methyl (2R,3R)-2-azido-3-(4-(benzyloxy)phenyl)-3-hydroxypropanoate

Base Information

• Chemical Name: methyl (2R,3R)-2-azido-3-(4-(benzyloxy)phenyl)-3-hydroxypropanoate
• CAS No.: 1417985-90-0
• Molecular Formula: C₁₇H₁₇N₃O₄
• Molecular Weight: 327.34
• Mol file: 1417985-90-0.mol

Synonyms:methyl (2R,3R)-2-azido-3-(4-(benzyloxy)phenyl)-3-hydroxypropanoate

Chemical Property of methyl (2R,3R)-2-azido-3-(4-(benzyloxy)phenyl)-3-hydroxypropanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (2R,3R)-2-azido-3-(4-(benzyloxy)phenyl)-3-hydroxypropanoate

There total 5 articles about methyl (2R,3R)-2-azido-3-(4-(benzyloxy)phenyl)-3-hydroxypropanoate 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: 100.0%

methyl (2S,3R)-3-(4-(benzyloxy)phenyl)-3-hydroxy-2-(((2-nitrophenyl)sulfonyl)oxy)propanoate (1607826-46-9) → methyl (2R,3R)-2-azido-3-(4-(benzyloxy)phenyl)-3-hydroxypropanoate (1417985-90-0)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 23 - 50 ℃; Inert atmosphere;

DOI:10.1021/ja502744a

Reference yield:

methyl (2S,3R)-3-(4-(benzyloxy)phenyl)-2,3-dihydroxypropanoate (1607826-45-8) → methyl (2R,3R)-2-azido-3-(4-(benzyloxy)phenyl)-3-hydroxypropanoate (1417985-90-0)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine / dichloromethane / 6 h / 0 °C / Inert atmosphere

2: sodium azide / N,N-dimethyl-formamide / 23 - 50 °C / Inert atmosphere

With sodium azide; triethylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja502744a

Reference yield:

benzyl bromide (100-39-0) → methyl (2R,3R)-2-azido-3-(4-(benzyloxy)phenyl)-3-hydroxypropanoate (1417985-90-0)

Guidance literature:

Multi-step reaction with 4 steps

1: potassium carbonate / acetone / 4 h / 23 °C / Reflux; Inert atmosphere

2: methanesulfonamide; AD-mix β / tert-butyl alcohol; water / 72 h / 0 °C / Inert atmosphere

3: triethylamine / dichloromethane / 6 h / 0 °C / Inert atmosphere

4: sodium azide / N,N-dimethyl-formamide / 23 - 50 °C / Inert atmosphere

With sodium azide; methanesulfonamide; AD-mix β; potassium carbonate; triethylamine; In dichloromethane; water; N,N-dimethyl-formamide; acetone; tert-butyl alcohol;

DOI:10.1021/ja502744a

upstream raw materials:

methyl (2S,3R)-3-(4-(benzyloxy)phenyl)-2,3-dihydroxypropanoate

methyl (2S,3R)-3-(4-(benzyloxy)phenyl)-3-hydroxy-2-(((2-nitrophenyl)sulfonyl)oxy)propanoate

benzyl bromide

methyl 4-hydroxycinnamate

Downstream raw materials:

methyl (2R,3R)-2-amino-3-(4-hydroxyphenyl)-3-methoxypropanoate

methyl (2R,3R)-2-(((allyloxy)carbonyl)amino)-3-(4-hydroxyphenyl)-3-methoxypropanoate

methyl (2R,3R)-2-(((allyloxy)carbonyl)amino)-3-methoxy-3-(4-(trityloxy)phenyl)propanoate

(2R,3R)-2-(((allyloxy)carbonyl)amino)-3-methoxy-3-(4-(trityloxy)phenyl)propanoic acid