(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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Chemical Name:(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
CAS No.:869494-44-0
Molecular Formula:C₃₁H₄₂N₄O₇
Molecular Weight:582.697
Hs Code.:

(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

Synonyms:(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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Chemical Property of (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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Technology Process of (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

There total 22 articles about (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 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: 83.0%

: 869494-42-8
(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

: 869494-44-0
(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

Guidance literature:: With hydrogen fluoride; In tetrahydrofuran; at 20 ℃; for 1h;
DOI:10.1021/jm050548m

Reference yield:

: 6525-53-7,16422-27-8,40149-68-6
L-glutamic acid dimethyl ester

: 869494-44-0
(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

Guidance literature:: Multi-step reaction with 12 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

10.1: TFA / CH₂Cl₂ / 0.5 h / 0 °C

11.1: HOBt; EDCI / CH₂Cl₂ / 0.17 h

11.2: 87.3 mg / DIPEA / CH₂Cl₂

12.1: 83 percent / aq. HF / tetrahydrofuran / 1 h / 20 °C

With lithium borohydride; hydrogen fluoride; 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:

: 56-86-0,21675-62-7,23009-64-5,25104-13-6,84960-48-5,25513-46-6
L-glutamic acid

: 869494-44-0
(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

Guidance literature:: Multi-step reaction with 13 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

11.1: TFA / CH₂Cl₂ / 0.5 h / 0 °C

12.1: HOBt; EDCI / CH₂Cl₂ / 0.17 h

12.2: 87.3 mg / DIPEA / CH₂Cl₂

13.1: 83 percent / aq. HF / tetrahydrofuran / 1 h / 20 °C

With lithium borohydride; chloro-trimethyl-silane; hydrogen fluoride; 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