methyl (2R,3R)-2-acetoxy-3-acetylamino-4-phenylbutyrate

Base Information

• Chemical Name: methyl (2R,3R)-2-acetoxy-3-acetylamino-4-phenylbutyrate
• CAS No.: 140409-03-6
• Molecular Formula: C₁₅H₁₉NO₅
• Molecular Weight: 293.32
• Mol file: 140409-03-6.mol

Synonyms:

Chemical Property of methyl (2R,3R)-2-acetoxy-3-acetylamino-4-phenylbutyrate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (2R,3R)-2-acetoxy-3-acetylamino-4-phenylbutyrate

There total 8 articles about methyl (2R,3R)-2-acetoxy-3-acetylamino-4-phenylbutyrate 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:

D-(R)-phenylalanine (673-06-3,25191-15-5,658-69-5,67675-33-6) → methyl (2R,3R)-2-acetoxy-3-acetylamino-4-phenylbutyrate (140409-03-6)

Guidance literature:

Multi-step reaction with 8 steps

1: 100 percent / SOCl₂

2: 89 percent / tetrahydrofuran / 1 h / 0 °C

3: 98 percent / LiCl, NaBH₄ / ethanol / 17 h / Ambient temperature

4: 81 percent / SO₃*Py, Et₃N / toluene; dimethylsulfoxide / 0.33 h / Ambient temperature

5: 100 percent / benzyltributylammonium chloride / CH₂Cl₂; H₂O / 3 h / 0 °C

6: 100 percent / aq. HCl / ethyl acetate / 14 h / 80 - 100 °C

7: SOCl₂ / a) RT, 1 h, b) reflux, 3 h

8: DMAP, pyridine / 16 h / Ambient temperature

With pyridine; hydrogenchloride; dmap; sodium tetrahydroborate; thionyl chloride; pyridine-SO₃ complex; benzyltri(n-butyl)ammonium chloride; triethylamine; lithium chloride; In tetrahydrofuran; ethanol; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; toluene;

DOI:10.1246/bcsj.65.360

Reference yield:

D-phenylalanine methyl ester hydrochloride (13033-84-6) → methyl (2R,3R)-2-acetoxy-3-acetylamino-4-phenylbutyrate (140409-03-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 89 percent / tetrahydrofuran / 1 h / 0 °C

2: 98 percent / LiCl, NaBH₄ / ethanol / 17 h / Ambient temperature

3: 81 percent / SO₃*Py, Et₃N / toluene; dimethylsulfoxide / 0.33 h / Ambient temperature

4: 100 percent / benzyltributylammonium chloride / CH₂Cl₂; H₂O / 3 h / 0 °C

5: 100 percent / aq. HCl / ethyl acetate / 14 h / 80 - 100 °C

6: SOCl₂ / a) RT, 1 h, b) reflux, 3 h

7: DMAP, pyridine / 16 h / Ambient temperature

With pyridine; hydrogenchloride; dmap; sodium tetrahydroborate; thionyl chloride; pyridine-SO₃ complex; benzyltri(n-butyl)ammonium chloride; triethylamine; lithium chloride; In tetrahydrofuran; ethanol; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; toluene;

DOI:10.1246/bcsj.65.360

Reference yield:

(R)-N-(isopropoxycarbonyl)phenylalaninal (129867-98-7) → methyl (2R,3R)-2-acetoxy-3-acetylamino-4-phenylbutyrate (140409-03-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 100 percent / benzyltributylammonium chloride / CH₂Cl₂; H₂O / 3 h / 0 °C

2: 100 percent / aq. HCl / ethyl acetate / 14 h / 80 - 100 °C

3: SOCl₂ / a) RT, 1 h, b) reflux, 3 h

4: DMAP, pyridine / 16 h / Ambient temperature

With pyridine; hydrogenchloride; dmap; thionyl chloride; benzyltri(n-butyl)ammonium chloride; In dichloromethane; water; ethyl acetate;

DOI:10.1246/bcsj.65.360

upstream raw materials:

acetic anhydride

(R)-3-Amino-2-hydroxy-4-phenyl-butyric acid methyl ester

D-(R)-phenylalanine

D-phenylalanine methyl ester hydrochloride

Refernces