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

Base Information

• Chemical Name: (2S,3R)-2-Amino-3-(tert-butyl-dimethyl-silanyloxy)-3-(3-chloro-4-hydroxy-phenyl)-propionic acid ethyl ester
• CAS No.: 218912-07-3
• Molecular Formula: C₁₇H₂₈ClNO₄Si
• Molecular Weight: 373.952

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

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

Chemical Property:

Purity/Quality:

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

There total 11 articles about (2S,3R)-2-Amino-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: 80.0%

(2S,3R)-2-Amino-3-(tert-butyl-dimethyl-silanyloxy)-3-(4-hydroxy-phenyl)-propionic acid ethyl ester (218912-06-2) → (2S,3R)-2-Amino-3-(tert-butyl-dimethyl-silanyloxy)-3-(3-chloro-4-hydroxy-phenyl)-propionic acid ethyl ester (218912-07-3)

Guidance literature:

With sulfuryl dichloride; In diethyl ether; dichloromethane; at 0 ℃; for 1h;

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

Reference yield:

(E)-ethyl 3-(4-(benzyloxy)phenyl)acrylate (104315-07-3) → (2S,3R)-2-Amino-3-(tert-butyl-dimethyl-silanyloxy)-3-(3-chloro-4-hydroxy-phenyl)-propionic acid ethyl ester (218912-07-3)

Guidance literature:

Multi-step reaction with 4 steps

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

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

3: 97 percent / H₂ / 20 percent Pd(OH)2 / methanol / 0.5 h / 25 °C

4: 80 percent / SO₂Cl₂ / diethyl ether; CH₂Cl₂ / 1 h / 0 °C

With 2,6-dimethylpyridine; sodium hydroxide; sulfuryl dichloride; tert-butylhypochlorite; water; hydrogen; palladium dihydroxide; potassium dioxotetrahydroxoosmate(VI); hydroquinidine anthraquinone-1,4-diyl diether; In methanol; propan-1-ol; diethyl ether; dichloromethane; 1: Addition / 2: Etherification / 3: Hydrogenolysis / 4: Chlorination;

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-Amino-3-(tert-butyl-dimethyl-silanyloxy)-3-(3-chloro-4-hydroxy-phenyl)-propionic acid ethyl ester (218912-07-3)

Guidance literature:

Multi-step reaction with 5 steps

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

2: 45 percent / NaOH; H₂O; t-BuOCl / (DHQD)2AQN; K₂2(OH)4> / propan-1-ol / 12 h / 25 °C

3: 98 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

4: 95 percent / H₂ / 10 percent Pd(OH)2/C / methanol / 0.5 h

5: SO₂Cl₂ / diethyl ether; CH₂Cl₂ / 1 h / 0 °C

With 2,6-dimethylpyridine; potassium hydroxide; sodium hydroxide; sulfuryl dichloride; tert-butylhypochlorite; water; hydrogen; palladium dihydroxide; hydroquinidine anthraquinone-1,4-diyl diether; K2; In tetrahydrofuran; methanol; propan-1-ol; diethyl ether; dichloromethane; 1: Wittig reaction / 2: Addition / 3: Etherification / 4: Hydrogenolysis / 5: Chlorination;

DOI:10.1002/(SICI)1521-3773(19981016)37:19<2708::AID-ANIE2708>3.0.CO;2-E

upstream raw materials:

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

p-benzyloxybenzaldehyde

4-hydroxy-benzaldehyde

(E)-ethyl 3-(4-(benzyloxy)phenyl)acrylate

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