(3S)-3-benzyloxycarbonyl-3-[(3S)-3-benzyloxycarbonyl-3-(tert-butyldiphenylsilyloxy)propanoyloxy]propanoic acid

Base Information

• Chemical Name: (3S)-3-benzyloxycarbonyl-3-[(3S)-3-benzyloxycarbonyl-3-(tert-butyldiphenylsilyloxy)propanoyloxy]propanoic acid
• CAS No.: 276871-02-4
• Molecular Formula: C₃₈H₄₀O₉Si
• Molecular Weight: 668.816
• Mol file: 276871-02-4.mol

Synonyms:(3S)-3-benzyloxycarbonyl-3-[(3S)-3-benzyloxycarbonyl-3-(tert-butyldiphenylsilyloxy)propanoyloxy]propanoic acid

Chemical Property of (3S)-3-benzyloxycarbonyl-3-[(3S)-3-benzyloxycarbonyl-3-(tert-butyldiphenylsilyloxy)propanoyloxy]propanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S)-3-benzyloxycarbonyl-3-[(3S)-3-benzyloxycarbonyl-3-(tert-butyldiphenylsilyloxy)propanoyloxy]propanoic acid

There total 6 articles about (3S)-3-benzyloxycarbonyl-3-[(3S)-3-benzyloxycarbonyl-3-(tert-butyldiphenylsilyloxy)propanoyloxy]propanoic 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: 93.0%

4-allyl 1-benzyl (2S)-2-[(3S)-3-benzyloxycarbonyl-3-(tert-butyldiphenylsilyloxy)propanoyloxy]butanedioate (276871-00-2) → (3S)-3-benzyloxycarbonyl-3-[(3S)-3-benzyloxycarbonyl-3-(tert-butyldiphenylsilyloxy)propanoyloxy]propanoic acid (276871-02-4)

Guidance literature:

With morpholine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1002/1099-0690(200004)2000:7<1207::AID-EJOC1207>3.0.CO;2-2

Reference yield:

(S)-3-(Benzyloxycarbonyl)-3-hydroxypropanoic acid (66178-04-9) → (3S)-3-benzyloxycarbonyl-3-[(3S)-3-benzyloxycarbonyl-3-(tert-butyldiphenylsilyloxy)propanoyloxy]propanoic acid (276871-02-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 92 percent / K₂CO₃; tetrabutyl ammonium bromide / dimethylformamide / 4 h / 20 °C

2: 5.96 g / pyridine / CH₂Cl₂ / -78 - 20 °C

3: 93 percent / morpholine / Pd(PPh₃)4 / tetrahydrofuran / 2 h / 20 °C

With morpholine; pyridine; tetrabutylammomium bromide; potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 1: Esterification / 2: Substitution / 3: Ester cleavage;

DOI:10.1002/1099-0690(200004)2000:7<1207::AID-EJOC1207>3.0.CO;2-2

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → (3S)-3-benzyloxycarbonyl-3-[(3S)-3-benzyloxycarbonyl-3-(tert-butyldiphenylsilyloxy)propanoyloxy]propanoic acid (276871-02-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: DMAP / dimethylformamide / 28 h / 20 °C

1.2: 80 percent / TFA / tetrahydrofuran; H₂O / 2 h / 0 - 20 °C

2.1: oxalyl chloride; DMF / CH₂Cl₂ / 20 °C

3.1: 5.96 g / pyridine / CH₂Cl₂ / -78 - 20 °C

4.1: 93 percent / morpholine / Pd(PPh₃)4 / tetrahydrofuran / 2 h / 20 °C

With morpholine; pyridine; dmap; oxalyl dichloride; N,N-dimethyl-formamide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 1.1: Esterification / 1.2: Hydrolysis / 2.1: Substitution / 3.1: Substitution / 4.1: Ester cleavage;

DOI:10.1002/1099-0690(200004)2000:7<1207::AID-EJOC1207>3.0.CO;2-2

upstream raw materials:

4-allyl 1-benzyl (2S)-2-[(3S)-3-benzyloxycarbonyl-3-(tert-butyldiphenylsilyloxy)propanoyloxy]butanedioate

(S)-3-(Benzyloxycarbonyl)-3-hydroxypropanoic acid

tert-butylchlorodiphenylsilane

4-allyl 1-benzyl (2S)-2-hydroxybutanedioate

Downstream raw materials:

(S)-2-(tert-Butyl-diphenyl-silanyloxy)-succinic acid 1-benzyl ester 4-{(S)-1-benzyloxycarbonyl-2-[(S)-1-benzyloxycarbonyl-2-((S)-1-benzyloxycarbonyl-2-carboxy-ethoxycarbonyl)-ethoxycarbonyl]-ethyl} ester

(S)-2-(tert-Butyl-diphenyl-silanyloxy)-succinic acid 4-{(S)-2-[(S)-2-((S)-2-allyloxycarbonyl-1-benzyloxycarbonyl-ethoxycarbonyl)-1-benzyloxycarbonyl-ethoxycarbonyl]-1-benzyloxycarbonyl-ethyl} ester 1-benzyl ester

(S)-2-(tert-Butyl-diphenyl-silanyloxy)-succinic acid 1-benzyl ester 4-{(S)-1-benzyloxycarbonyl-2-[(S)-1-benzyloxycarbonyl-2-((S)-1,2-bis-benzyloxycarbonyl-ethoxycarbonyl)-ethoxycarbonyl]-ethyl} ester