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

Base Information

• Chemical Name: tert-butyl (R,R)-2-methanesulfonyloxy-3-[N-(tert-butoxycarbonyl)amino]-3-phenylpropanoate
• CAS No.: 1454771-29-9
• Molecular Formula: C₁₉H₂₉NO₇S
• Molecular Weight: 415.508
• Mol file: 1454771-29-9.mol

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

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

There total 4 articles about tert-butyl (R,R)-2-methanesulfonyloxy-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: 86.0%

tert-butyl (R,R)-2-hydroxy-3-[N-(tert-butoxycarbonyl)amino]-3-phenylpropanoate (1454771-27-7) + methanesulfonyl chloride (124-63-0) → tert-butyl (R,R)-2-methanesulfonyloxy-3-[N-(tert-butoxycarbonyl)amino]-3-phenylpropanoate (1454771-29-9)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃; for 15h; Inert atmosphere;

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 (R,R)-2-methanesulfonyloxy-3-[N-(tert-butoxycarbonyl)amino]-3-phenylpropanoate (1454771-29-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 10 wt% Pd(OH)2 on carbon; hydrogen / ethyl acetate / 15 h / 20 °C / 3800.26 Torr

2: triethylamine; dmap / dichloromethane / 15 h / 20 °C / Inert atmosphere

With dmap; 10 wt% Pd(OH)2 on carbon; hydrogen; triethylamine; In dichloromethane; ethyl acetate;

DOI:10.1016/j.tet.2013.08.007

Reference yield:

tert-butyl cinnamate (14990-09-1) → tert-butyl (R,R)-2-methanesulfonyloxy-3-[N-(tert-butoxycarbonyl)amino]-3-phenylpropanoate (1454771-29-9)

Guidance literature:

Multi-step reaction with 3 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: 10 wt% Pd(OH)2 on carbon; hydrogen / ethyl acetate / 15 h / 20 °C / 3800.26 Torr

3.1: triethylamine; dmap / dichloromethane / 15 h / 20 °C / Inert atmosphere

With dmap; n-butyllithium; 10 wt% Pd(OH)2 on carbon; hydrogen; triethylamine; In tetrahydrofuran; hexane; dichloromethane; ethyl acetate;

DOI:10.1016/j.tet.2013.08.007

upstream raw materials:

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

tert-butyl cinnamate

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

methanesulfonyl chloride

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

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

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