(E)-(4R,5S)-4-Benzyloxy-5-[(S)-3-(tert-butyl-dimethyl-silanyloxy)-butyryloxy]-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-[(S)-3-(tert-butyl-dimethyl-silanyloxy)-butyryloxy]-hex-2-enoic acid (E)-(1S,2R)-2-benzyloxy-1-methyl-4-(2,2,2-trichloro-ethoxycarbonyl)-but-3-enyl ester
CAS No.:294198-54-2
Molecular Formula:C₃₈H₅₁Cl₃O₉Si
Molecular Weight:786.262
Hs Code.:

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

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

Suppliers and Price of (E)-(4R,5S)-4-Benzyloxy-5-[(S)-3-(tert-butyl-dimethyl-silanyloxy)-butyryloxy]-hex-2-enoic acid (E)-(1S,2R)-2-benzyloxy-1-methyl-4-(2,2,2-trichloro-ethoxycarbonyl)-but-3-enyl ester

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

Total 0 raw suppliers

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

There total 9 articles about (E)-(4R,5S)-4-Benzyloxy-5-[(S)-3-(tert-butyl-dimethyl-silanyloxy)-butyryloxy]-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: 79.0%

: 101515-46-2,107493-76-5,105729-41-7
(S)-3-[(tert-butyldimethylsilyl)oxy]butanoic acid

: 294198-52-0
(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

: 294198-54-2
(E)-(4R,5S)-4-Benzyloxy-5-[(S)-3-(tert-butyl-dimethyl-silanyloxy)-butyryloxy]-hex-2-enoic acid (E)-(1S,2R)-2-benzyloxy-1-methyl-4-(2,2,2-trichloro-ethoxycarbonyl)-but-3-enyl ester

Guidance literature:: With dmap; (+)-comphorsulfonic acid; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 48h;
DOI:10.1016/S0957-4166(00)00245-7

Reference yield:

: 183625-29-8
methyl (4R,5S)-4-benzyloxy-5-hydroxy-2(E)-hexenoate

: 294198-54-2
(E)-(4R,5S)-4-Benzyloxy-5-[(S)-3-(tert-butyl-dimethyl-silanyloxy)-butyryloxy]-hex-2-enoic acid (E)-(1S,2R)-2-benzyloxy-1-methyl-4-(2,2,2-trichloro-ethoxycarbonyl)-but-3-enyl ester

Guidance literature:: Multi-step reaction with 7 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

6: 79 percent / aq. AcOH / tetrahydrofuran / 48 h / 80 °C

7: 79 percent / DCC; DMAP; (+)-comphorsulfonic acid / CH₂Cl₂ / 48 h / 20 °C

With 1H-imidazole; dmap; sodium hydroxide; (+)-comphorsulfonic acid; 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 / 6: desilylation / 7: Keck esterification;
DOI:10.1016/S0957-4166(00)00245-7

Reference yield:

: 294198-49-5
(4R,5S)-4-benzyloxy-5-tert-butyldimethylsilyloxy-2(E)-hexenoic acid

: 294198-54-2
(E)-(4R,5S)-4-Benzyloxy-5-[(S)-3-(tert-butyl-dimethyl-silanyloxy)-butyryloxy]-hex-2-enoic acid (E)-(1S,2R)-2-benzyloxy-1-methyl-4-(2,2,2-trichloro-ethoxycarbonyl)-but-3-enyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: DCC; DMAP / CH₂Cl₂ / 72 h / 20 °C

2: 87 percent / aq. AcOH / tetrahydrofuran / 15 h / 70 - 110 °C

3: 75 percent / DCC; (+)-camphorsulfonic acid; DMAP / CH₂Cl₂ / 48 h / 20 °C

4: 79 percent / aq. AcOH / tetrahydrofuran / 48 h / 80 °C

5: 79 percent / DCC; DMAP; (+)-comphorsulfonic acid / CH₂Cl₂ / 48 h / 20 °C

With dmap; (+)-comphorsulfonic acid; acetic acid; (+)-10-camphorsulfonic acid; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; 1: Esterification / 2: desilylation / 3: Keck esterification / 4: desilylation / 5: Keck esterification;
DOI:10.1016/S0957-4166(00)00245-7