(2S,3R)-2-Allyloxycarbonylamino-3-(4-allyloxy-3-chloro-phenyl)-3-hydroxy-propionic acid

Base Information

• Chemical Name: (2S,3R)-2-Allyloxycarbonylamino-3-(4-allyloxy-3-chloro-phenyl)-3-hydroxy-propionic acid
• CAS No.: 851968-85-9
• Molecular Formula: C₁₆H₁₈ClNO₆
• Molecular Weight: 355.775
• Mol file: 851968-85-9.mol

Synonyms:

Chemical Property of (2S,3R)-2-Allyloxycarbonylamino-3-(4-allyloxy-3-chloro-phenyl)-3-hydroxy-propionic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-2-Allyloxycarbonylamino-3-(4-allyloxy-3-chloro-phenyl)-3-hydroxy-propionic acid

There total 5 articles about (2S,3R)-2-Allyloxycarbonylamino-3-(4-allyloxy-3-chloro-phenyl)-3-hydroxy-propionic acid 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:

(4S,5R)-5-(4-Allyloxy-3-chloro-phenyl)-2-thioxo-oxazolidine-4-carboxylic acid methyl ester (851968-84-8) + Allyl chloroformate (2937-50-0) → (4S,5R)-5-(4-Allyloxy-3-chloro-phenyl)-2-oxo-oxazolidine-4-carboxylic acid + (2S,3R)-2-Allyloxycarbonylamino-3-(4-allyloxy-3-chloro-phenyl)-3-hydroxy-propionic acid (851968-85-9)

Guidance literature:

(4S,5R)-5-(4-Allyloxy-3-chloro-phenyl)-2-thioxo-oxazolidine-4-carboxylic acid methyl ester; Allyl chloroformate; With dmap; triethylamine; In dichloromethane; at 20 ℃; for 1.5h;

With formic acid; dihydrogen peroxide; In dichloromethane; at 0 ℃; for 0.5h;

With lithium hydroxide; In 1,4-dioxane; at 20 ℃; for 1.5h;

DOI:10.1039/b418908f

Reference yield:

(S)-3-[(4S,5R)-5-(4-Allyloxy-3-chloro-phenyl)-2-thioxo-oxazolidine-4-carbonyl]-4-benzyl-oxazolidin-2-one → (2S,3R)-2-Allyloxycarbonylamino-3-(4-allyloxy-3-chloro-phenyl)-3-hydroxy-propionic acid (851968-85-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 87 percent / MeMgBr / CH₂Cl₂; diethyl ether / 0.05 h / 0 °C

2.1: DMAP; Et₃N / CH₂Cl₂ / 1.5 h / 20 °C

2.2: aq. H₂O₂; formic acid / CH₂Cl₂ / 0.5 h / 0 °C

2.3: 240 mg / aq. LiOH / dioxane / 1.5 h / 20 °C

With dmap; methylmagnesium bromide; triethylamine; In diethyl ether; dichloromethane;

DOI:10.1039/b418908f

Reference yield:

4-hydroxy-3-chlorobenzaldehyde (2420-16-8) → (2S,3R)-2-Allyloxycarbonylamino-3-(4-allyloxy-3-chloro-phenyl)-3-hydroxy-propionic acid (851968-85-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 3.7 g / K₂CO₃ / acetone / 4 h / Heating

2.1: Sn(OTf)2; N-ethylpiperidine / tetrahydrofuran / 1.5 h / -78 °C

2.2: 81 percent / tetrahydrofuran / 3 h / -78 °C

3.1: 87 percent / MeMgBr / CH₂Cl₂; diethyl ether / 0.05 h / 0 °C

4.1: DMAP; Et₃N / CH₂Cl₂ / 1.5 h / 20 °C

4.2: aq. H₂O₂; formic acid / CH₂Cl₂ / 0.5 h / 0 °C

4.3: 240 mg / aq. LiOH / dioxane / 1.5 h / 20 °C

With 1-ethyl-piperidine; dmap; tin(II) trifluoromethanesulfonate; methylmagnesium bromide; potassium carbonate; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; acetone;

DOI:10.1039/b418908f

upstream raw materials:

(4S,5R)-5-(4-Allyloxy-3-chloro-phenyl)-2-thioxo-oxazolidine-4-carboxylic acid methyl ester

Allyl chloroformate

4-hydroxy-3-chlorobenzaldehyde

4-allyloxy-3-chloro-benzaldehyde