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

Base Information

• Chemical Name: tert-butyl (2S,3R)-2-methanesulfonyloxy-3-[N-(tert-butoxycarbonyl)amino]-3-phenylpropanoate
• CAS No.: 1454771-35-7
• Molecular Formula: C₁₉H₂₉NO₇S
• Molecular Weight: 415.508

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of tert-butyl (2S,3R)-2-methanesulfonyloxy-3-[N-(tert-butoxycarbonyl)amino]-3-phenylpropanoate

There total 5 articles about tert-butyl (2S,3R)-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: 95.0%

tert-butyl (2S,3R)-2-hydroxy-3-[N-(tert-butoxycarbonyl)amino]-3-phenylpropanoate (1454771-33-5) + methanesulfonyl chloride (124-63-0) → tert-butyl (2S,3R)-2-methanesulfonyloxy-3-[N-(tert-butoxycarbonyl)amino]-3-phenylpropanoate (1454771-35-7)

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 cinnamate (14990-09-1) → tert-butyl (2S,3R)-2-methanesulfonyloxy-3-[N-(tert-butoxycarbonyl)amino]-3-phenylpropanoate (1454771-35-7)

Guidance literature:

Multi-step reaction with 5 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: methanol; sodium tetrahydroborate / 2 h / -20 °C / Inert atmosphere

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

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

With methanol; dmap; sodium tetrahydroborate; n-butyllithium; oxalyl dichloride; 10 wt% Pd(OH)2 on carbon; hydrogen; dimethyl sulfoxide; triethylamine; 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-methanesulfonyloxy-3-[N-(tert-butoxycarbonyl)amino]-3-phenylpropanoate (1454771-35-7)

Guidance literature:

Multi-step reaction with 4 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

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

With dmap; oxalyl dichloride; 10 wt% Pd(OH)2 on carbon; hydrogen; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; 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 (2S,3R)-2-hydroxy-3-[N-(tert-butoxycarbonyl)amino]-3-phenylpropanoate

methanesulfonyl chloride

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

tert-butyl cinnamate

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

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