(E)-(4R,5S)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-hex-2-enoic acid (E)-(1S,2R)-2-benzyloxy-1-methyl-4-(2,2,2-trichloro-ethoxycarbonyl)-but-3-enyl ester

Base Information

• Chemical Name: (E)-(4R,5S)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-hex-2-enoic acid (E)-(1S,2R)-2-benzyloxy-1-methyl-4-(2,2,2-trichloro-ethoxycarbonyl)-but-3-enyl ester
• CAS No.: 294198-51-9
• Molecular Formula: C₃₄H₄₅Cl₃O₇Si
• Molecular Weight: 700.172
• Mol file: 294198-51-9.mol

Synonyms:(E)-(4R,5S)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-hex-2-enoic acid (E)-(1S,2R)-2-benzyloxy-1-methyl-4-(2,2,2-trichloro-ethoxycarbonyl)-but-3-enyl ester

Chemical Property of (E)-(4R,5S)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-hex-2-enoic acid (E)-(1S,2R)-2-benzyloxy-1-methyl-4-(2,2,2-trichloro-ethoxycarbonyl)-but-3-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(4R,5S)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-hex-2-enoic acid (E)-(1S,2R)-2-benzyloxy-1-methyl-4-(2,2,2-trichloro-ethoxycarbonyl)-but-3-enyl ester

There total 6 articles about (E)-(4R,5S)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-hex-2-enoic acid (E)-(1S,2R)-2-benzyloxy-1-methyl-4-(2,2,2-trichloro-ethoxycarbonyl)-but-3-enyl 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%

2,2,2-trichloroethyl (4R,5S)-4-benzyloxy-5-hydroxy-2(E)-hexenoate (294198-50-8) + (4R,5S)-4-benzyloxy-5-tert-butyldimethylsilyloxy-2(E)-hexenoic acid (294198-49-5) → (E)-(4R,5S)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-hex-2-enoic acid (E)-(1S,2R)-2-benzyloxy-1-methyl-4-(2,2,2-trichloro-ethoxycarbonyl)-but-3-enyl ester (294198-51-9)

Guidance literature:

With dmap; (+)-10-camphorsulfonic acid; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 48h;

DOI:10.1016/S0957-4166(00)00245-7

Reference yield:

methyl (4R,5S)-4-benzyloxy-5-hydroxy-2(E)-hexenoate (183625-29-8) → (E)-(4R,5S)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-hex-2-enoic acid (E)-(1S,2R)-2-benzyloxy-1-methyl-4-(2,2,2-trichloro-ethoxycarbonyl)-but-3-enyl ester (294198-51-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 98 percent / imidazole / dimethylformamide / 2.5 h / 0 - 20 °C

2: 2M aq. NaOH / methanol / 12 h / 20 °C

3: DCC; DMAP / CH₂Cl₂ / 72 h / 20 °C

4: 87 percent / aq. AcOH / tetrahydrofuran / 15 h / 70 - 110 °C

5: 75 percent / DCC; (+)-camphorsulfonic acid; DMAP / CH₂Cl₂ / 48 h / 20 °C

With 1H-imidazole; dmap; sodium hydroxide; acetic acid; (+)-10-camphorsulfonic acid; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 1: silylation / 2: Hydrolysis / 3: Esterification / 4: desilylation / 5: Keck esterification;

DOI:10.1016/S0957-4166(00)00245-7

Reference yield:

methyl (4R,5S)-4-benzyloxy-5-tert-butyldimethylsilyloxy-2(E)-hexenoate (294198-48-4) → (E)-(4R,5S)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-hex-2-enoic acid (E)-(1S,2R)-2-benzyloxy-1-methyl-4-(2,2,2-trichloro-ethoxycarbonyl)-but-3-enyl ester (294198-51-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 2M aq. NaOH / methanol / 12 h / 20 °C

2: DCC; DMAP / CH₂Cl₂ / 72 h / 20 °C

3: 87 percent / aq. AcOH / tetrahydrofuran / 15 h / 70 - 110 °C

4: 75 percent / DCC; (+)-camphorsulfonic acid; DMAP / CH₂Cl₂ / 48 h / 20 °C

With dmap; sodium hydroxide; acetic acid; (+)-10-camphorsulfonic acid; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; dichloromethane; 1: Hydrolysis / 2: Esterification / 3: desilylation / 4: Keck esterification;

DOI:10.1016/S0957-4166(00)00245-7

upstream raw materials:

2,2,2-trichloroethyl (4R,5S)-4-benzyloxy-5-hydroxy-2(E)-hexenoate

(4R,5S)-4-benzyloxy-5-tert-butyldimethylsilyloxy-2(E)-hexenoic acid

tert-butyldimethylsilyl chloride

methyl (4R,5S)-4-benzyloxy-5-hydroxy-2(E)-hexenoate

Downstream raw materials:

(E)-(4R,5S)-4-Benzyloxy-5-hydroxy-hex-2-enoic acid (E)-(1S,2R)-2-benzyloxy-1-methyl-4-(2,2,2-trichloro-ethoxycarbonyl)-but-3-enyl ester

(+)-macrosphelide A

(-)-dibenzyl macrosphelide A

(E)-(4R,5S)-4-Benzyloxy-5-[(E)-(4R,5S)-4-benzyloxy-5-((S)-3-hydroxy-butyryloxy)-hex-2-enoyloxy]-hex-2-enoic acid