(E)-(S)-4-[(2R,4S,5S)-2-Benzyl-5-tert-butoxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-6-methyl-heptanoylamino]-5-((S)-2-oxo-pyrrolidin-3-yl)-pent-2-enoic acid ethyl ester

Base Information

• Chemical Name: (E)-(S)-4-[(2R,4S,5S)-2-Benzyl-5-tert-butoxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-6-methyl-heptanoylamino]-5-((S)-2-oxo-pyrrolidin-3-yl)-pent-2-enoic acid ethyl ester
• CAS No.: 869494-40-6
• Molecular Formula: C₃₇H₆₁N₃O₇Si
• Molecular Weight: 687.993

Synonyms:(E)-(S)-4-[(2R,4S,5S)-2-Benzyl-5-tert-butoxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-6-methyl-heptanoylamino]-5-((S)-2-oxo-pyrrolidin-3-yl)-pent-2-enoic acid ethyl ester

Chemical Property of (E)-(S)-4-[(2R,4S,5S)-2-Benzyl-5-tert-butoxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-6-methyl-heptanoylamino]-5-((S)-2-oxo-pyrrolidin-3-yl)-pent-2-enoic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of (E)-(S)-4-[(2R,4S,5S)-2-Benzyl-5-tert-butoxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-6-methyl-heptanoylamino]-5-((S)-2-oxo-pyrrolidin-3-yl)-pent-2-enoic acid ethyl ester

There total 15 articles about (E)-(S)-4-[(2R,4S,5S)-2-Benzyl-5-tert-butoxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-6-methyl-heptanoylamino]-5-((S)-2-oxo-pyrrolidin-3-yl)-pent-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:

L-glutamic acid dimethyl ester (6525-53-7,16422-27-8,40149-68-6) → (E)-(S)-4-[(2R,4S,5S)-2-Benzyl-5-tert-butoxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-6-methyl-heptanoylamino]-5-((S)-2-oxo-pyrrolidin-3-yl)-pent-2-enoic acid ethyl ester (869494-40-6)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 5.55 g / Et₃N / methanol / 1 h

2.1: LHMDS / hexane; tetrahydrofuran / 1 h / -78 °C

2.2: 79 percent / hexane; tetrahydrofuran / 2 h / -78 °C

3.1: H₂ / PtO₂ / CHCl₃; methanol / 36 h / 2585.74 Torr

4.1: 4.2 g / Na₂CO₃ / CHCl₃; methanol / 6 h / pH 7 / Heating

5.1: 91 percent / LiBH₄ / CH₂Cl₂; tetrahydrofuran / 1.5 h / 23 °C

6.1: pyridine*SO₃; DMSO; Et₃N / CH₂Cl₂ / 2 h / 0 - 23 °C

7.1: 191 mg / CH₂Cl₂ / 2 h / 23 °C

8.1: TFA / CH₂Cl₂ / 1 h / 0 °C

9.1: HOBt; EDCI / CH₂Cl₂ / 0.17 h

9.2: 111 mg / DIPEA / CH₂Cl₂

With lithium borohydride; hydrogen; sulfur trioxide pyridine complex; sodium carbonate; benzotriazol-1-ol; dimethyl sulfoxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; lithium hexamethyldisilazane; platinum(IV) oxide; In tetrahydrofuran; methanol; hexane; dichloromethane; chloroform; 7.1: Wittig reaction;

DOI:10.1021/jm050548m

Reference yield:

L-glutamic acid (56-86-0,21675-62-7,23009-64-5,25104-13-6,84960-48-5,25513-46-6) → (E)-(S)-4-[(2R,4S,5S)-2-Benzyl-5-tert-butoxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-6-methyl-heptanoylamino]-5-((S)-2-oxo-pyrrolidin-3-yl)-pent-2-enoic acid ethyl ester (869494-40-6)

Guidance literature:

Multi-step reaction with 10 steps

1.1: Me₃SiCl / 0 - 23 °C

2.1: 5.55 g / Et₃N / methanol / 1 h

3.1: LHMDS / hexane; tetrahydrofuran / 1 h / -78 °C

3.2: 79 percent / hexane; tetrahydrofuran / 2 h / -78 °C

4.1: H₂ / PtO₂ / CHCl₃; methanol / 36 h / 2585.74 Torr

5.1: 4.2 g / Na₂CO₃ / CHCl₃; methanol / 6 h / pH 7 / Heating

6.1: 91 percent / LiBH₄ / CH₂Cl₂; tetrahydrofuran / 1.5 h / 23 °C

7.1: pyridine*SO₃; DMSO; Et₃N / CH₂Cl₂ / 2 h / 0 - 23 °C

8.1: 191 mg / CH₂Cl₂ / 2 h / 23 °C

9.1: TFA / CH₂Cl₂ / 1 h / 0 °C

10.1: HOBt; EDCI / CH₂Cl₂ / 0.17 h

10.2: 111 mg / DIPEA / CH₂Cl₂

With lithium borohydride; chloro-trimethyl-silane; hydrogen; sulfur trioxide pyridine complex; sodium carbonate; benzotriazol-1-ol; dimethyl sulfoxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; lithium hexamethyldisilazane; platinum(IV) oxide; In tetrahydrofuran; methanol; hexane; dichloromethane; chloroform; 8.1: Wittig reaction;

DOI:10.1021/jm050548m

Reference yield:

dimethyl (2S)-2-[(tert-butoxycarbonyl)amino]pentanedioate (59279-60-6,130622-05-8,861658-15-3) → (E)-(S)-4-[(2R,4S,5S)-2-Benzyl-5-tert-butoxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-6-methyl-heptanoylamino]-5-((S)-2-oxo-pyrrolidin-3-yl)-pent-2-enoic acid ethyl ester (869494-40-6)

Guidance literature:

Multi-step reaction with 8 steps

1.1: LHMDS / hexane; tetrahydrofuran / 1 h / -78 °C

1.2: 79 percent / hexane; tetrahydrofuran / 2 h / -78 °C

2.1: H₂ / PtO₂ / CHCl₃; methanol / 36 h / 2585.74 Torr

3.1: 4.2 g / Na₂CO₃ / CHCl₃; methanol / 6 h / pH 7 / Heating

4.1: 91 percent / LiBH₄ / CH₂Cl₂; tetrahydrofuran / 1.5 h / 23 °C

5.1: pyridine*SO₃; DMSO; Et₃N / CH₂Cl₂ / 2 h / 0 - 23 °C

6.1: 191 mg / CH₂Cl₂ / 2 h / 23 °C

7.1: TFA / CH₂Cl₂ / 1 h / 0 °C

8.1: HOBt; EDCI / CH₂Cl₂ / 0.17 h

8.2: 111 mg / DIPEA / CH₂Cl₂

With lithium borohydride; hydrogen; sulfur trioxide pyridine complex; sodium carbonate; benzotriazol-1-ol; dimethyl sulfoxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; lithium hexamethyldisilazane; platinum(IV) oxide; In tetrahydrofuran; methanol; hexane; dichloromethane; chloroform; 6.1: Wittig reaction;

DOI:10.1021/jm050548m

upstream raw materials:

(2R,4S,5S)-2-benzyl-5-{[(tert-butoxy)carbonyl]amino}-4-[(tertbutyldimethylsilyl)oxy]-6-methylheptanoic acid

ethyl (S,E)-4-((tert-butoxycarbonyl)amino)-5-((S)-2-oxopyrrolidin-3-yl)pent-2-enoate

L-glutamic acid

L-glutamic acid dimethyl ester

Downstream raw materials:

(E)-(S)-4-{(2R,4S,5S)-2-Benzyl-4-(tert-butyl-dimethyl-silanyloxy)-6-methyl-5-[(5-methyl-isoxazole-3-carbonyl)-amino]-heptanoylamino}-5-((S)-2-oxo-pyrrolidin-3-yl)-pent-2-enoic acid ethyl ester

(E)-(S)-4-{(2R,4S,5S)-2-Benzyl-4-hydroxy-6-methyl-5-[(5-methyl-isoxazole-3-carbonyl)-amino]-heptanoylamino}-5-((S)-2-oxo-pyrrolidin-3-yl)-pent-2-enoic acid ethyl ester

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