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

Base Information

• Chemical Name: (2S,3R)-2-Benzyloxycarbonylamino-3-(4-benzyloxy-phenyl)-3-(tert-butyl-dimethyl-silanyloxy)-propionic acid ethyl ester
• CAS No.: 218912-05-1
• Molecular Formula: C₃₂H₄₁NO₆Si
• Molecular Weight: 563.766

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

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

There total 5 articles about (2S,3R)-2-Benzyloxycarbonylamino-3-(4-benzyloxy-phenyl)-3-(tert-butyl-dimethyl-silanyloxy)-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:

p-benzyloxybenzaldehyde (4397-53-9) → (2S,3R)-2-Benzyloxycarbonylamino-3-(4-benzyloxy-phenyl)-3-(tert-butyl-dimethyl-silanyloxy)-propionic acid ethyl ester (218912-05-1)

Guidance literature:

Multi-step reaction with 3 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

With 2,6-dimethylpyridine; potassium hydroxide; sodium hydroxide; tert-butylhypochlorite; water; potassium dioxotetrahydroxoosmate(VI); hydroquinidine anthraquinone-1,4-diyl diether; In tetrahydrofuran; propan-1-ol; dichloromethane; 1: Condensation / 2: Addition / 3: Etherification;

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

Reference yield:

benzyl bromide (100-39-0) → (2S,3R)-2-Benzyloxycarbonylamino-3-(4-benzyloxy-phenyl)-3-(tert-butyl-dimethyl-silanyloxy)-propionic acid ethyl ester (218912-05-1)

Guidance literature:

Multi-step reaction with 4 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

With 2,6-dimethylpyridine; potassium hydroxide; sodium hydroxide; tert-butylhypochlorite; water; potassium carbonate; potassium iodide; potassium dioxotetrahydroxoosmate(VI); hydroquinidine anthraquinone-1,4-diyl diether; In tetrahydrofuran; propan-1-ol; dichloromethane; N,N-dimethyl-formamide; 1: Etherification / 2: Condensation / 3: Addition / 4: Etherification;

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-Benzyloxycarbonylamino-3-(4-benzyloxy-phenyl)-3-(tert-butyl-dimethyl-silanyloxy)-propionic acid ethyl ester (218912-05-1)

Guidance literature:

Multi-step reaction with 4 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

With 2,6-dimethylpyridine; potassium hydroxide; sodium hydroxide; tert-butylhypochlorite; water; potassium carbonate; potassium iodide; potassium dioxotetrahydroxoosmate(VI); hydroquinidine anthraquinone-1,4-diyl diether; In tetrahydrofuran; propan-1-ol; dichloromethane; N,N-dimethyl-formamide; 1: Etherification / 2: Condensation / 3: Addition / 4: Etherification;

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

upstream raw materials:

t-butyldimethylsiyl triflate

p-benzyloxybenzaldehyde

benzyl bromide

4-hydroxy-benzaldehyde

Downstream raw materials:

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

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

(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

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

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