(2S,3R)-2-[(R)-2-Amino-2-(4-methoxy-phenyl)-acetylamino]-3-(tert-butyl-dimethyl-silanyloxy)-3-(3-chloro-4-hydroxy-phenyl)-propionic acid ethyl ester

Base Information

• Chemical Name: (2S,3R)-2-[(R)-2-Amino-2-(4-methoxy-phenyl)-acetylamino]-3-(tert-butyl-dimethyl-silanyloxy)-3-(3-chloro-4-hydroxy-phenyl)-propionic acid ethyl ester
• CAS No.: 250249-08-2
• Molecular Formula: C₂₆H₃₇ClN₂O₆Si
• Molecular Weight: 537.128
• Mol file: 250249-08-2.mol

Synonyms:(2S,3R)-2-[(R)-2-Amino-2-(4-methoxy-phenyl)-acetylamino]-3-(tert-butyl-dimethyl-silanyloxy)-3-(3-chloro-4-hydroxy-phenyl)-propionic acid ethyl ester

Chemical Property of (2S,3R)-2-[(R)-2-Amino-2-(4-methoxy-phenyl)-acetylamino]-3-(tert-butyl-dimethyl-silanyloxy)-3-(3-chloro-4-hydroxy-phenyl)-propionic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-2-[(R)-2-Amino-2-(4-methoxy-phenyl)-acetylamino]-3-(tert-butyl-dimethyl-silanyloxy)-3-(3-chloro-4-hydroxy-phenyl)-propionic acid ethyl ester

There total 12 articles about (2S,3R)-2-[(R)-2-Amino-2-(4-methoxy-phenyl)-acetylamino]-3-(tert-butyl-dimethyl-silanyloxy)-3-(3-chloro-4-hydroxy-phenyl)-propionic acid ethyl ester 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: 75.0%

2-[2-tert-butoxycarbonylamino-2-(4-methoxy-phenyl)-acetylamino]-3-(tert-butyl-dimethyl-silanyloxy)-3-(3-chloro-4-hydroxy-phenyl)-propionic acid ethyl ester (250249-07-1) → (2S,3R)-2-[(R)-2-Amino-2-(4-methoxy-phenyl)-acetylamino]-3-(tert-butyl-dimethyl-silanyloxy)-3-(3-chloro-4-hydroxy-phenyl)-propionic acid ethyl ester (250249-08-2)

Guidance literature:

With 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -10 ℃; for 1h;

DOI:10.1002/(SICI)1521-3765(19990903)5:9<2602::AID-CHEM2602>3.0.CO;2-X

Reference yield:

p-benzyloxybenzaldehyde (4397-53-9) → (2S,3R)-2-[(R)-2-Amino-2-(4-methoxy-phenyl)-acetylamino]-3-(tert-butyl-dimethyl-silanyloxy)-3-(3-chloro-4-hydroxy-phenyl)-propionic acid ethyl ester (250249-08-2)

Guidance literature:

Multi-step reaction with 7 steps

1: 95 percent / KOH / tetrahydrofuran / 12 h / 25 °C

2: 45 percent / NaOH; t-BuOCl; H₂O / (DHQD)2AQN; K₂OsO₂(OH)4 / propan-1-ol / 12 h / 25 °C

3: 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

4: 97 percent / H₂ / 20 percent Pd(OH)2 / methanol / 0.5 h / 25 °C

5: 81 percent / HOBt; EDC / dimethylformamide / 12 h / -20 - 0 °C

6: 88 percent / SO₂Cl₂ / diethyl ether; CH₂Cl₂ / 0.5 h / 0 °C

7: 75 percent / TMSOTf; 2,6-lutidine / CH₂Cl₂ / 1 h / -10 °C

With 2,6-dimethylpyridine; potassium hydroxide; sodium hydroxide; sulfuryl dichloride; tert-butylhypochlorite; trimethylsilyl trifluoromethanesulfonate; water; hydrogen; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; palladium dihydroxide; potassium dioxotetrahydroxoosmate(VI); hydroquinidine anthraquinone-1,4-diyl diether; In tetrahydrofuran; methanol; propan-1-ol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 1: Condensation / 2: Addition / 3: Etherification / 4: Hydrogenolysis / 5: Acylation / 6: Chlorination / 7: Substitution;

DOI:10.1002/(SICI)1521-3765(19990903)5:9<2602::AID-CHEM2602>3.0.CO;2-X

Reference yield:

4-hydroxy-benzaldehyde (123-08-0,65581-83-1) → (2S,3R)-2-[(R)-2-Amino-2-(4-methoxy-phenyl)-acetylamino]-3-(tert-butyl-dimethyl-silanyloxy)-3-(3-chloro-4-hydroxy-phenyl)-propionic acid ethyl ester (250249-08-2)

Guidance literature:

Multi-step reaction with 8 steps

1: 98 percent / K₂CO₃; KI / dimethylformamide / 12 h / 25 °C

2: 95 percent / KOH / tetrahydrofuran / 12 h / 25 °C

3: 45 percent / NaOH; t-BuOCl; H₂O / (DHQD)2AQN; K₂OsO₂(OH)4 / propan-1-ol / 12 h / 25 °C

4: 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

5: 97 percent / H₂ / 20 percent Pd(OH)2 / methanol / 0.5 h / 25 °C

6: 81 percent / HOBt; EDC / dimethylformamide / 12 h / -20 - 0 °C

7: 88 percent / SO₂Cl₂ / diethyl ether; CH₂Cl₂ / 0.5 h / 0 °C

8: 75 percent / TMSOTf; 2,6-lutidine / CH₂Cl₂ / 1 h / -10 °C

With 2,6-dimethylpyridine; potassium hydroxide; sodium hydroxide; sulfuryl dichloride; tert-butylhypochlorite; trimethylsilyl trifluoromethanesulfonate; water; hydrogen; potassium carbonate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; potassium iodide; palladium dihydroxide; potassium dioxotetrahydroxoosmate(VI); hydroquinidine anthraquinone-1,4-diyl diether; In tetrahydrofuran; methanol; propan-1-ol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 1: Etherification / 2: Condensation / 3: Addition / 4: Etherification / 5: Hydrogenolysis / 6: Acylation / 7: Chlorination / 8: Substitution;

DOI:10.1002/(SICI)1521-3765(19990903)5:9<2602::AID-CHEM2602>3.0.CO;2-X

upstream raw materials:

2-[2-tert-butoxycarbonylamino-2-(4-methoxy-phenyl)-acetylamino]-3-(tert-butyl-dimethyl-silanyloxy)-3-(3-chloro-4-hydroxy-phenyl)-propionic acid ethyl ester

p-benzyloxybenzaldehyde

(R)-tert-butoxycarbonylamino-[4-methoxy-phenyl]-acetic acid

D-2-p-hydroxyphenylglycine methyl ester

Downstream raw materials:

(2S,3R)-2-[(R)-2-{(R)-2-tert-Butoxycarbonylamino-2-[3,5-dibromo-4-(pyrrolidin-1-ylazo)-phenyl]-acetylamino}-2-(4-methoxy-phenyl)-acetylamino]-3-(tert-butyl-dimethyl-silanyloxy)-3-(3-chloro-4-hydroxy-phenyl)-propionic acid ethyl ester