(2S,3R)-ethyl 2-((S)-2-(tert-butoxycarbonylamino)propanamido)-3-methoxy-3-phenylpropanoate

Base Information

• Chemical Name: (2S,3R)-ethyl 2-((S)-2-(tert-butoxycarbonylamino)propanamido)-3-methoxy-3-phenylpropanoate
• CAS No.: 1345116-55-3
• Molecular Formula: C₂₀H₃₀N₂O₆
• Molecular Weight: 394.468
• Mol file: 1345116-55-3.mol

Synonyms:(2S,3R)-ethyl 2-((S)-2-(tert-butoxycarbonylamino)propanamido)-3-methoxy-3-phenylpropanoate

Chemical Property of (2S,3R)-ethyl 2-((S)-2-(tert-butoxycarbonylamino)propanamido)-3-methoxy-3-phenylpropanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-ethyl 2-((S)-2-(tert-butoxycarbonylamino)propanamido)-3-methoxy-3-phenylpropanoate

There total 3 articles about (2S,3R)-ethyl 2-((S)-2-(tert-butoxycarbonylamino)propanamido)-3-methoxy-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%

(2S,3R)-ethyl 2-((S)-2-(tert-butoxycarbonylamino)propanamido)-3-hydroxy-3-phenylpropanoate (1346156-35-1) + methyl iodide (74-88-4) → (2S,3R)-ethyl 2-((S)-2-(tert-butoxycarbonylamino)propanamido)-3-methoxy-3-phenylpropanoate (1345116-55-3)

Guidance literature:

With silver(l) oxide; In tetrahydrofuran; at 45 ℃; for 48h; Inert atmosphere; Darkness;

DOI:10.1016/j.tetasy.2011.08.026

Reference yield:

(2S,3R)-2-amino-3-hydroxy-3-phenyl-propionic acid ethyl ester (911475-69-9) → (2S,3R)-ethyl 2-((S)-2-(tert-butoxycarbonylamino)propanamido)-3-methoxy-3-phenylpropanoate (1345116-55-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 0 °C / Inert atmosphere

1.2: 24 h / 20 °C / Inert atmosphere

2.1: silver(l) oxide / tetrahydrofuran / 48 h / 45 °C / Inert atmosphere; Darkness

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; silver(l) oxide; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tetasy.2011.08.026

Reference yield:

L-N-Boc-Ala (15761-38-3) → (2S,3R)-ethyl 2-((S)-2-(tert-butoxycarbonylamino)propanamido)-3-methoxy-3-phenylpropanoate (1345116-55-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 0 °C / Inert atmosphere

1.2: 24 h / 20 °C / Inert atmosphere

2.1: silver(l) oxide / tetrahydrofuran / 48 h / 45 °C / Inert atmosphere; Darkness

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; silver(l) oxide; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tetasy.2011.08.026

upstream raw materials:

(2S,3R)-ethyl 2-((S)-2-(tert-butoxycarbonylamino)propanamido)-3-hydroxy-3-phenylpropanoate

methyl iodide

L-N-Boc-Ala

(2S,3R)-2-amino-3-hydroxy-3-phenyl-propionic acid ethyl ester

Downstream raw materials:

(6S,9R,12S)-methyl 6-((R)-3-(benzoyloxy)-2-methylpropyl)-12-((R)-methoxy(phenyl)methyl)-2,2,5,9-tetramethyl-4,7,10-trioxo-3-oxa-5,8,11-triazatridecan-13-oate

(6R,8S,11S,14S)-8-(tert-butoxycarbonyl(methyl)amino)-14-((R)-methoxy(phenyl)methyl)-2,2,6,11-tetramethyl-9,12-dioxo-3,3-diphenyl-4-oxa-10,13-diaza-3-silapentadecan-15-oic acid

(6R,8S,11R,14S)-methyl 8-(tert-butoxycarbonyl(methyl)amino)-14-((R)-methoxy(phenyl)methyl)-2,2,6,11-tetramethyl-9,12-dioxo-3,3-diphenyl-4-oxa-10,13-diaza-3-silapentadecan-15-oate

C₂HF₃O₂*C₁₅H₂₂N₂O₄