N,N-[(2S,3R)-2-benzyloxycarbonylamino-3-(2-benzyloxyphenyl)-3-hydroxypropionyl]-β-alanyl-β-alanine

Base Information

• Chemical Name: N,N-[(2S,3R)-2-benzyloxycarbonylamino-3-(2-benzyloxyphenyl)-3-hydroxypropionyl]-β-alanyl-β-alanine
• CAS No.: 444154-84-1
• Molecular Formula: C₃₀H₃₃N₃O₈
• Molecular Weight: 563.607
• Mol file: 444154-84-1.mol

Synonyms:N,N-[(2S,3R)-2-benzyloxycarbonylamino-3-(2-benzyloxyphenyl)-3-hydroxypropionyl]-β-alanyl-β-alanine

Chemical Property of N,N-[(2S,3R)-2-benzyloxycarbonylamino-3-(2-benzyloxyphenyl)-3-hydroxypropionyl]-β-alanyl-β-alanine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N,N-[(2S,3R)-2-benzyloxycarbonylamino-3-(2-benzyloxyphenyl)-3-hydroxypropionyl]-β-alanyl-β-alanine

There total 7 articles about N,N-[(2S,3R)-2-benzyloxycarbonylamino-3-(2-benzyloxyphenyl)-3-hydroxypropionyl]-β-alanyl-β-alanine 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: 84.0%

N,N-[(2S,3R)-2-benzyloxycarbonylamino-3-(2-benzyloxyphenyl)-3-hydroxypropionyl]-β-alanyl-β-alanine methyl ester (444154-81-8) → N,N-[(2S,3R)-2-benzyloxycarbonylamino-3-(2-benzyloxyphenyl)-3-hydroxypropionyl]-β-alanyl-β-alanine (444154-84-1)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; water; at 0 ℃; for 1h;

DOI:10.1021/jo0256078

Reference yield:

3-(2-hydroxy-phenyl)-acrylic acid ethyl ester (3943-94-0,6236-62-0,17041-46-2) → N,N-[(2S,3R)-2-benzyloxycarbonylamino-3-(2-benzyloxyphenyl)-3-hydroxypropionyl]-β-alanyl-β-alanine (444154-84-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.490 g / K₂CO₃ / dimethylformamide / 20 °C

2: NaOh; t-BuOCl; (DHQD)2AQN / K₂[OsO₂(OH)4] / H₂O; propan-1-ol / 2 h / 20 °C

3: 93 percent / LiOH / tetrahydrofuran; H₂O / 1 h / 0 °C

4: 54 percent / HOAt; EDC; DMAP / CH₂Cl₂ / 20 °C

5: 84 percent / LiOH / tetrahydrofuran; H₂O / 1 h / 0 °C

With dmap; lithium hydroxide; sodium hydroxide; 1-hydroxy-7-aza-benzotriazole; hydroquinidine anthraquinone-1,4-diyl diether; tert-butylhypochlorite; potassium carbonate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; K2; In tetrahydrofuran; propan-1-ol; dichloromethane; water; N,N-dimethyl-formamide; 2: Sharpless asymmetric aminohydroxylation;

DOI:10.1021/jo0256078

Reference yield:

2-hydroxycinnamic acid (495-79-4,583-17-5,614-60-8) → N,N-[(2S,3R)-2-benzyloxycarbonylamino-3-(2-benzyloxyphenyl)-3-hydroxypropionyl]-β-alanyl-β-alanine (444154-84-1)

Guidance literature:

Multi-step reaction with 6 steps

1: conc. H₂SO₄ / 5 h / Heating

2: 1.490 g / K₂CO₃ / dimethylformamide / 20 °C

3: NaOh; t-BuOCl; (DHQD)2AQN / K₂[OsO₂(OH)4] / H₂O; propan-1-ol / 2 h / 20 °C

4: 93 percent / LiOH / tetrahydrofuran; H₂O / 1 h / 0 °C

5: 54 percent / HOAt; EDC; DMAP / CH₂Cl₂ / 20 °C

6: 84 percent / LiOH / tetrahydrofuran; H₂O / 1 h / 0 °C

With dmap; lithium hydroxide; sodium hydroxide; 1-hydroxy-7-aza-benzotriazole; hydroquinidine anthraquinone-1,4-diyl diether; tert-butylhypochlorite; sulfuric acid; potassium carbonate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; K2; In tetrahydrofuran; propan-1-ol; dichloromethane; water; N,N-dimethyl-formamide; 3: Sharpless asymmetric aminohydroxylation;

DOI:10.1021/jo0256078

upstream raw materials:

N,N-[(2S,3R)-2-benzyloxycarbonylamino-3-(2-benzyloxyphenyl)-3-hydroxypropionyl]-β-alanyl-β-alanine methyl ester

3-(2-hydroxy-phenyl)-acrylic acid ethyl ester

2-hydroxycinnamic acid

(2E)-3-(2-benzyloxy-phenyl)-acrylic acid ethyl ester