tert-butyl (2S,3R)-2-hydroxy-3-[N-(tert-butoxycarbonyl)amino]-3-phenylpropanoate

Base Information

• Chemical Name: tert-butyl (2S,3R)-2-hydroxy-3-[N-(tert-butoxycarbonyl)amino]-3-phenylpropanoate
• CAS No.: 1454771-33-5
• Molecular Formula: C₁₈H₂₇NO₅
• Molecular Weight: 337.416
• Mol file: 1454771-33-5.mol

Synonyms:tert-butyl (2S,3R)-2-hydroxy-3-[N-(tert-butoxycarbonyl)amino]-3-phenylpropanoate

Chemical Property of tert-butyl (2S,3R)-2-hydroxy-3-[N-(tert-butoxycarbonyl)amino]-3-phenylpropanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (2S,3R)-2-hydroxy-3-[N-(tert-butoxycarbonyl)amino]-3-phenylpropanoate

There total 4 articles about tert-butyl (2S,3R)-2-hydroxy-3-[N-(tert-butoxycarbonyl)amino]-3-phenylpropanoate 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%

di-tert-butyl dicarbonate (24424-99-5) + tert-butyl (2S,3R,αR)-3--2-hydroxy-3-phenylpropionate → tert-butyl (2S,3R)-2-hydroxy-3-[N-(tert-butoxycarbonyl)amino]-3-phenylpropanoate (1454771-33-5)

Guidance literature:

With 10 wt% Pd(OH)2 on carbon; hydrogen; In ethyl acetate; at 20 ℃; for 15h; under 3800.26 Torr;

DOI:10.1016/j.tet.2013.08.007

Reference yield:

tert-butyl cinnamate (14990-09-1) → tert-butyl (2S,3R)-2-hydroxy-3-[N-(tert-butoxycarbonyl)amino]-3-phenylpropanoate (1454771-33-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: n-butyllithium / hexane; tetrahydrofuran / -78 °C / Inert atmosphere

1.2: 2 h / -78 °C / Inert atmosphere

1.3: 15 h / 20 °C / Inert atmosphere

2.1: dimethyl sulfoxide; oxalyl dichloride / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

2.2: 0.5 h / -78 - 20 °C / Inert atmosphere

3.1: diisobutylaluminium hydride / tetrahydrofuran / 2 h / -20 °C / Inert atmosphere

3.2: -20 - 20 °C / Inert atmosphere

3.3: 15 h / 20 °C

4.1: 10 wt% Pd(OH)2 on carbon; hydrogen / ethyl acetate / 15 h / 20 °C / 3800.26 Torr

With n-butyllithium; oxalyl dichloride; 10 wt% Pd(OH)2 on carbon; hydrogen; diisobutylaluminium hydride; dimethyl sulfoxide; In tetrahydrofuran; hexane; dichloromethane; ethyl acetate; 2.1: |Swern Oxidation / 2.2: |Swern Oxidation;

DOI:10.1016/j.tet.2013.08.007

Reference yield:

tert-butyl (2R,3R,αR)-3--2-hydroxy-3-phenylpropionate (151671-03-3) → tert-butyl (2S,3R)-2-hydroxy-3-[N-(tert-butoxycarbonyl)amino]-3-phenylpropanoate (1454771-33-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: dimethyl sulfoxide; oxalyl dichloride / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

1.2: 0.5 h / -78 - 20 °C / Inert atmosphere

2.1: diisobutylaluminium hydride / tetrahydrofuran / 2 h / -20 °C / Inert atmosphere

2.2: -20 - 20 °C / Inert atmosphere

2.3: 15 h / 20 °C

3.1: 10 wt% Pd(OH)2 on carbon; hydrogen / ethyl acetate / 15 h / 20 °C / 3800.26 Torr

With oxalyl dichloride; 10 wt% Pd(OH)2 on carbon; hydrogen; diisobutylaluminium hydride; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane; ethyl acetate; 1.1: |Swern Oxidation / 1.2: |Swern Oxidation;

DOI:10.1016/j.tet.2013.08.007

upstream raw materials:

tert-butyl (2R,3R,αR)-3--2-hydroxy-3-phenylpropionate

tert-butyl cinnamate

di-tert-butyl dicarbonate

tert-butyl (3R,αR)-3--2-oxo-3-phenylpropionate

Downstream raw materials:

di-tert-butyl (2S,3R)-3-phenylaziridine-N⁽¹⁾,2-dicarboxylate

di-tert-butyl (R,R)-3-phenylaziridine-N⁽¹⁾,2-dicarboxylate

(R,R)-5-phenyl-4-(tert-butoxycarbonyl)oxazolidin-2-one

C₁₄H₁₇NO₄