(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

Base Information

• Chemical Name: (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
• CAS No.: 276871-03-5
• Molecular Formula: C₆₃H₆₄O₁₇Si
• Molecular Weight: 1121.28
• Mol file: 276871-03-5.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 8 articles about (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 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:

4-allyl 1-benzyl (2S)-2-[(3S)-3-benzyloxycarbonyl-3-(tert-butyldiphenylsilyloxy)propanoyloxy]butanedioate (276871-00-2) → (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 (276871-03-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / 70percent HF / CH₂Cl₂; pyridine / 14 h / 0 - 20 °C

2: 2.71 g / pyridine / CH₂Cl₂ / -78 - 20 °C

With pyridine; In pyridine; dichloromethane; 1: Hydrolysis / 2: Condensation;

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

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → (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 (276871-03-5)

Guidance literature:

Multi-step reaction with 6 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

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

6.1: 2.71 g / pyridine / CH₂Cl₂ / -78 - 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 / 5.1: Substitution / 6.1: Condensation;

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

Reference yield:

2-(tert-butyl-diphenyl-silanyloxy)-3-chlorocarbonyl-propionic acid benzyl 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 (276871-03-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 5.96 g / pyridine / CH₂Cl₂ / -78 - 20 °C

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

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

4: 2.71 g / pyridine / CH₂Cl₂ / -78 - 20 °C

With morpholine; pyridine; oxalyl dichloride; N,N-dimethyl-formamide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; dichloromethane; 1: Substitution / 2: Ester cleavage / 3: Substitution / 4: Condensation;

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-hydroxypropanoyloxy]butanedioate

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

tert-butylchlorodiphenylsilane

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

Downstream raw materials:

(S)-2-{(S)-3-[(S)-3-((S)-3-Acetoxy-3-benzyloxycarbonyl-propionyloxy)-3-benzyloxycarbonyl-propionyloxy]-3-benzyloxycarbonyl-propionyloxy}-succinic acid 1-benzyl ester

(S)-2-[(S)-3-((S)-3-Acetoxy-3-benzyloxycarbonyl-propionyloxy)-3-benzyloxycarbonyl-propionyloxy]-succinic acid 4-((S)-2-allyloxycarbonyl-1-benzyloxycarbonyl-ethyl) ester 1-benzyl ester

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