(E)-(S)-4-((2R,5S)-2-Benzyl-5-tert-butoxycarbonylamino-6-methyl-4-oxo-heptanoylamino)-6-(trityl-carbamoyl)-hex-2-enoic acid ethyl ester

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Chemical Name:(E)-(S)-4-((2R,5S)-2-Benzyl-5-tert-butoxycarbonylamino-6-methyl-4-oxo-heptanoylamino)-6-(trityl-carbamoyl)-hex-2-enoic acid ethyl ester
CAS No.:214286-43-8
Molecular Formula:C₄₈H₅₇N₃O₇
Molecular Weight:787.996
Hs Code.:

Synonyms:(E)-(S)-4-((2R,5S)-2-Benzyl-5-tert-butoxycarbonylamino-6-methyl-4-oxo-heptanoylamino)-6-(trityl-carbamoyl)-hex-2-enoic acid ethyl ester

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Chemical Property of (E)-(S)-4-((2R,5S)-2-Benzyl-5-tert-butoxycarbonylamino-6-methyl-4-oxo-heptanoylamino)-6-(trityl-carbamoyl)-hex-2-enoic acid ethyl ester

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Technology Process of (E)-(S)-4-((2R,5S)-2-Benzyl-5-tert-butoxycarbonylamino-6-methyl-4-oxo-heptanoylamino)-6-(trityl-carbamoyl)-hex-2-enoic acid ethyl ester

There total 9 articles about (E)-(S)-4-((2R,5S)-2-Benzyl-5-tert-butoxycarbonylamino-6-methyl-4-oxo-heptanoylamino)-6-(trityl-carbamoyl)-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:

: 61229-07-0
trans-6-methylhept-4-enoic acid

: 214286-43-8
(E)-(S)-4-((2R,5S)-2-Benzyl-5-tert-butoxycarbonylamino-6-methyl-4-oxo-heptanoylamino)-6-(trityl-carbamoyl)-hex-2-enoic acid ethyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 41 percent / SOCl₂ / CHCl₃ / 0.75 h / Heating

2: 56 percent / Et₃N / tetrahydrofuran / 0.25 h / 0 °C

3: 1.) LDA, LiCl / 1.) THF, hexane, a) -78 deg C, 1.75 h, b) 0 deg C, 20 min, c) 23 deg C, 5 min, 2.) THF, 0 deg C, 30 min

4: N-bromosuccinimide, glacial AcOH / tetrahydrofuran; H₂O / a) 0 deg C, 15 min, b) reflux, 45 min

5: NaN₃ / dimethylformamide / 67 h / 50 °C

6: H₂ / 10 percent Pd/C / methanol / 16 h / 23 °C

7: aq. LiOH / 1,2-dimethoxy-ethane / 0.5 h / 23 °C

8: 4-methylmorpholine N-oxide, 4 A molecular sieves, tetrapropylammonium perruthenate / CH₂Cl₂ / 1.33 h / 23 °C

9: 4-methymorpholine, 1-hydroxybenzotriazole hydrate, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 19 h / 23 °C

With 4-methyl-morpholine; lithium hydroxide; N-Bromosuccinimide; thionyl chloride; sodium azide; tetrapropylammonium perruthennate; 4 A molecular sieve; hydrogen; acetic acid; 4-methylmorpholine N-oxide; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; lithium chloride; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; chloroform; water; N,N-dimethyl-formamide;
DOI:10.1021/jm980537b

Reference yield:

: 112375-59-4
trans-6-methylhept-4-enoic acid chloride

: 214286-43-8
(E)-(S)-4-((2R,5S)-2-Benzyl-5-tert-butoxycarbonylamino-6-methyl-4-oxo-heptanoylamino)-6-(trityl-carbamoyl)-hex-2-enoic acid ethyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 56 percent / Et₃N / tetrahydrofuran / 0.25 h / 0 °C

2: 1.) LDA, LiCl / 1.) THF, hexane, a) -78 deg C, 1.75 h, b) 0 deg C, 20 min, c) 23 deg C, 5 min, 2.) THF, 0 deg C, 30 min

3: N-bromosuccinimide, glacial AcOH / tetrahydrofuran; H₂O / a) 0 deg C, 15 min, b) reflux, 45 min

4: NaN₃ / dimethylformamide / 67 h / 50 °C

5: H₂ / 10 percent Pd/C / methanol / 16 h / 23 °C

6: aq. LiOH / 1,2-dimethoxy-ethane / 0.5 h / 23 °C

7: 4-methylmorpholine N-oxide, 4 A molecular sieves, tetrapropylammonium perruthenate / CH₂Cl₂ / 1.33 h / 23 °C

8: 4-methymorpholine, 1-hydroxybenzotriazole hydrate, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 19 h / 23 °C

With 4-methyl-morpholine; lithium hydroxide; N-Bromosuccinimide; sodium azide; tetrapropylammonium perruthennate; 4 A molecular sieve; hydrogen; acetic acid; 4-methylmorpholine N-oxide; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; lithium chloride; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/jm980537b

Reference yield:

: 179617-47-1
trans-6-methyl-hept-4-enoic acid ethyl ester

: 214286-43-8
(E)-(S)-4-((2R,5S)-2-Benzyl-5-tert-butoxycarbonylamino-6-methyl-4-oxo-heptanoylamino)-6-(trityl-carbamoyl)-hex-2-enoic acid ethyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: KOH / ethanol / 5 h / Heating

2: 41 percent / SOCl₂ / CHCl₃ / 0.75 h / Heating

3: 56 percent / Et₃N / tetrahydrofuran / 0.25 h / 0 °C

4: 1.) LDA, LiCl / 1.) THF, hexane, a) -78 deg C, 1.75 h, b) 0 deg C, 20 min, c) 23 deg C, 5 min, 2.) THF, 0 deg C, 30 min

5: N-bromosuccinimide, glacial AcOH / tetrahydrofuran; H₂O / a) 0 deg C, 15 min, b) reflux, 45 min

6: NaN₃ / dimethylformamide / 67 h / 50 °C

7: H₂ / 10 percent Pd/C / methanol / 16 h / 23 °C

8: aq. LiOH / 1,2-dimethoxy-ethane / 0.5 h / 23 °C

9: 4-methylmorpholine N-oxide, 4 A molecular sieves, tetrapropylammonium perruthenate / CH₂Cl₂ / 1.33 h / 23 °C

10: 4-methymorpholine, 1-hydroxybenzotriazole hydrate, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 19 h / 23 °C

With 4-methyl-morpholine; potassium hydroxide; lithium hydroxide; N-Bromosuccinimide; thionyl chloride; sodium azide; tetrapropylammonium perruthennate; 4 A molecular sieve; hydrogen; acetic acid; 4-methylmorpholine N-oxide; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; lithium chloride; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; ethanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide;
DOI:10.1021/jm980537b