(E)-(4R,5S)-6-(tert-Butyl-dimethyl-silanyloxy)-4-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-propionylamino]-2,5-dimethyl-hex-2-enoic acid ethyl ester

Base Information

• Chemical Name: (E)-(4R,5S)-6-(tert-Butyl-dimethyl-silanyloxy)-4-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-propionylamino]-2,5-dimethyl-hex-2-enoic acid ethyl ester
• CAS No.: 328381-80-2
• Molecular Formula: C₃₅H₅₅NO₅Si₂
• Molecular Weight: 625.996

Synonyms:(E)-(4R,5S)-6-(tert-Butyl-dimethyl-silanyloxy)-4-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-propionylamino]-2,5-dimethyl-hex-2-enoic acid ethyl ester

Chemical Property of (E)-(4R,5S)-6-(tert-Butyl-dimethyl-silanyloxy)-4-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-propionylamino]-2,5-dimethyl-hex-2-enoic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

Useful:

Technology Process of (E)-(4R,5S)-6-(tert-Butyl-dimethyl-silanyloxy)-4-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-propionylamino]-2,5-dimethyl-hex-2-enoic acid ethyl ester

There total 10 articles about (E)-(4R,5S)-6-(tert-Butyl-dimethyl-silanyloxy)-4-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-propionylamino]-2,5-dimethyl-hex-2-enoic 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: 80.0%

(E)-(4R,5S)-4-{Benzyloxycarbonyl-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-propionyl]-amino}-6-(tert-butyl-dimethyl-silanyloxy)-2,5-dimethyl-hex-2-enoic acid ethyl ester → (E)-(4R,5S)-6-(tert-Butyl-dimethyl-silanyloxy)-4-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-propionylamino]-2,5-dimethyl-hex-2-enoic acid ethyl ester (328381-80-2)

Guidance literature:

With hydrogen; Pd-BaSO₄; In ethyl acetate; under 4137.18 Torr;

DOI:10.1002/1521-3773(20001215)39:24<4612::AID-ANIE4612>3.0.CO;2-C

Reference yield:

(4S,5R)-5-(tert-butyldiphenylsilyloxymethyl)-4-methyl-4,5-dihydrofuran (221007-97-2) → (E)-(4R,5S)-6-(tert-Butyl-dimethyl-silanyloxy)-4-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-propionylamino]-2,5-dimethyl-hex-2-enoic acid ethyl ester (328381-80-2)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 87 percent / H₂O / CH₂Cl₂ / 20 °C / Irradiation

2.1: 77 percent / toluene / Heating

3.1: 98 percent / TBAF / tetrahydrofuran

4.1: aq. NaIO₄ / tetrahydrofuran

5.1: NaBH₄ / CH₂Cl₂; methanol

6.1: imidazole / toluene

7.1: LiHMDS / tetrahydrofuran / -78 °C

7.2: 92 percent / tetrahydrofuran

8.1: 80 percent / H₂ / Pd/BaSO₄ / ethyl acetate / 4137.18 Torr

With 1H-imidazole; sodium tetrahydroborate; sodium periodate; tetrabutyl ammonium fluoride; water; hydrogen; lithium hexamethyldisilazane; Pd-BaSO₄; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; toluene;

DOI:10.1002/1521-3773(20001215)39:24<4612::AID-ANIE4612>3.0.CO;2-C

Reference yield:

(3S,4S,5R)-<5-(tert-butyldiphenylsilyloxymethyl)-2-hydroxy-4-methyltetrahydrofuran-3-yl>carbamic acid benzyl ester (221007-99-4) → (E)-(4R,5S)-6-(tert-Butyl-dimethyl-silanyloxy)-4-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-propionylamino]-2,5-dimethyl-hex-2-enoic acid ethyl ester (328381-80-2)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 77 percent / toluene / Heating

2.1: 98 percent / TBAF / tetrahydrofuran

3.1: aq. NaIO₄ / tetrahydrofuran

4.1: NaBH₄ / CH₂Cl₂; methanol

5.1: imidazole / toluene

6.1: LiHMDS / tetrahydrofuran / -78 °C

6.2: 92 percent / tetrahydrofuran

7.1: 80 percent / H₂ / Pd/BaSO₄ / ethyl acetate / 4137.18 Torr

With 1H-imidazole; sodium tetrahydroborate; sodium periodate; tetrabutyl ammonium fluoride; hydrogen; lithium hexamethyldisilazane; Pd-BaSO₄; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; toluene;

DOI:10.1002/1521-3773(20001215)39:24<4612::AID-ANIE4612>3.0.CO;2-C

upstream raw materials:

(4S,5R)-5-(tert-butyldiphenylsilyloxymethyl)-4-methyl-4,5-dihydrofuran

(3S,4S,5R)-<5-(tert-butyldiphenylsilyloxymethyl)-2-hydroxy-4-methyltetrahydrofuran-3-yl>carbamic acid benzyl ester

(2R,3S)-1-(tert-butyldiphenylsilyloxy)-3-methylpent-4-en-2-ol

tert-Butyl-((2R,3S)-3-methyl-2-vinyloxy-pent-4-enyloxy)-diphenyl-silane

Downstream raw materials:

N-{1-[2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-4-hydroxy-3-methyl-but-2-enyl}-2-(tert-butyl-diphenyl-silanyloxy)-propionamide

N-{4-bromo-1-[2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-3-methyl-but-2-enyl}-2-(tert-butyl-diphenyl-silanyloxy)-propionamide

(S)-N-[(E)-(R)-4-(Benzothiazole-2-sulfonyl)-1-((S)-2-hydroxy-1-methyl-ethyl)-3-methyl-but-2-enyl]-2-(tert-butyl-diphenyl-silanyloxy)-propionamide

N-{4-(benzothiazol-2-ylsulfanyl)-1-[2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-3-methyl-but-2-enyl}-2-(tert-butyl-diphenyl-silanyloxy)-propionamide

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