(S)-2-{3-[(R)-2-Acryloylamino-3-(4-methoxy-phenyl)-propionylamino]-propionyloxy}-4-methyl-pentanoic acid (S)-1-[(S)-1-((2R,3R)-3-phenyl-oxiranyl)-ethyl]-but-3-enyl ester

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Chemical Name:(S)-2-{3-[(R)-2-Acryloylamino-3-(4-methoxy-phenyl)-propionylamino]-propionyloxy}-4-methyl-pentanoic acid (S)-1-[(S)-1-((2R,3R)-3-phenyl-oxiranyl)-ethyl]-but-3-enyl ester
CAS No.:733769-83-0
Molecular Formula:C₃₆H₄₆N₂O₈
Molecular Weight:634.77
Hs Code.:

(S)-2-{3-[(R)-2-Acryloylamino-3-(4-methoxy-phenyl)-propionylamino]-propionyloxy}-4-methyl-pentanoic acid (S)-1-[(S)-1-((2R,3R)-3-phenyl-oxiranyl)-ethyl]-but-3-enyl ester

Synonyms:(S)-2-{3-[(R)-2-Acryloylamino-3-(4-methoxy-phenyl)-propionylamino]-propionyloxy}-4-methyl-pentanoic acid (S)-1-[(S)-1-((2R,3R)-3-phenyl-oxiranyl)-ethyl]-but-3-enyl ester

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Chemical Property of (S)-2-{3-[(R)-2-Acryloylamino-3-(4-methoxy-phenyl)-propionylamino]-propionyloxy}-4-methyl-pentanoic acid (S)-1-[(S)-1-((2R,3R)-3-phenyl-oxiranyl)-ethyl]-but-3-enyl ester

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Technology Process of (S)-2-{3-[(R)-2-Acryloylamino-3-(4-methoxy-phenyl)-propionylamino]-propionyloxy}-4-methyl-pentanoic acid (S)-1-[(S)-1-((2R,3R)-3-phenyl-oxiranyl)-ethyl]-but-3-enyl ester

There total 15 articles about (S)-2-{3-[(R)-2-Acryloylamino-3-(4-methoxy-phenyl)-propionylamino]-propionyloxy}-4-methyl-pentanoic acid (S)-1-[(S)-1-((2R,3R)-3-phenyl-oxiranyl)-ethyl]-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:

: 733769-84-1
(2S,3S)-2-((2R,3R)-3-Phenyl-oxiranyl)-hex-5-en-3-ol

: 1026015-46-2
(S)-2-{3-[(R)-2-Acryloylamino-3-(4-methoxy-phenyl)-propionylamino]-propionyloxy}-4-methyl-pentanoic acid

: 733769-83-0
(S)-2-{3-[(R)-2-Acryloylamino-3-(4-methoxy-phenyl)-propionylamino]-propionyloxy}-4-methyl-pentanoic acid (S)-1-[(S)-1-((2R,3R)-3-phenyl-oxiranyl)-ethyl]-but-3-enyl ester

Guidance literature:: (S)-2-{3-[(R)-2-Acryloylamino-3-(4-methoxy-phenyl)-propionylamino]-propionyloxy}-4-methyl-pentanoic acid; With dmap; 2,4,6-trichlorobenzoyl chloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 2h;

(2S,3S)-2-((2R,3R)-3-Phenyl-oxiranyl)-hex-5-en-3-ol; In dichloromethane; at 20 ℃; for 16h; Further stages.;
DOI:10.1016/j.tetlet.2004.04.164

Reference yield:

: 591-50-4
iodobenzene

: 733769-83-0
(S)-2-{3-[(R)-2-Acryloylamino-3-(4-methoxy-phenyl)-propionylamino]-propionyloxy}-4-methyl-pentanoic acid (S)-1-[(S)-1-((2R,3R)-3-phenyl-oxiranyl)-ethyl]-but-3-enyl ester

Guidance literature:: Multi-step reaction with 9 steps

1.1: 65 percent / Pd(OAc)2; Et₃N / acetonitrile / 12 h / Heating

2.1: 60 percent / K₂OsO₂(OH)4; K₃Fe(CN)6; (DHQD)2PHAL / 2-methyl-propan-2-ol; H₂O / 24 h / 20 °C

3.1: PPTS / CH₂Cl₂ / 3 h / 20 °C

4.1: CH₂Cl₂ / 6 h / 20 °C

5.1: 95 percent / K₂CO₃; MeOH / tetrahydrofuran / 8 h / 0 - 20 °C

6.1: Dess-Martin reagent / CH₂Cl₂ / 3 h / 0 - 20 °C

7.1: tetrahydrofuran / 2 h / 0 °C

8.1: nBu₄NF / tetrahydrofuran / 6 h / 20 °C

9.1: DIEA; DMAP; 2,4,6-trichlorobenzoyl chloride / CH₂Cl₂ / 2 h / 20 °C

9.2: CH₂Cl₂ / 16 h / 20 °C

With methanol; dmap; palladium diacetate; potassium dioxotetrahydroxoosmate(VI); 2,4,6-trichlorobenzoyl chloride; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; potassium carbonate; Dess-Martin periodane; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; N-ethyl-N,N-diisopropylamine; potassium hexacyanoferrate(III); In tetrahydrofuran; dichloromethane; water; acetonitrile; tert-butyl alcohol; 1.1: Heck coupling / 2.1: Sharpless asymmetric dihydroxylation / 6.1: Dess-Martin oxidation / 7.1: Tebbe olefination / 9.2: Yamaguchi coupling;
DOI:10.1016/j.tetlet.2004.04.164

Reference yield:

: 17355-19-0,61780-18-5,120349-74-8
methyl (R)-2-amino-3-(4-methoxyphenyl)propanoate

: 733769-83-0
(S)-2-{3-[(R)-2-Acryloylamino-3-(4-methoxy-phenyl)-propionylamino]-propionyloxy}-4-methyl-pentanoic acid (S)-1-[(S)-1-((2R,3R)-3-phenyl-oxiranyl)-ethyl]-but-3-enyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: DIEA / 2 h / 0 °C

2.1: LiOH / methanol; tetrahydrofuran; H₂O / 3 h / 20 °C

3.1: 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide*HCl; DMAP; 1-hydroxybenzotriazol / tetrahydrofuran; dimethylformamide / 2 h / 20 °C

3.2: tetrahydrofuran; dimethylformamide / 16 h / 20 °C

4.1: LiOH / methanol; tetrahydrofuran; H₂O / 3 h / 20 °C

5.1: 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide*HCl; DMAP / 2 h / 0 °C

5.2: 16 h / 20 °C

6.1: TFA / CH₂Cl₂ / 5 h / 20 °C

7.1: DIEA; DMAP; 2,4,6-trichlorobenzoyl chloride / CH₂Cl₂ / 2 h / 20 °C

7.2: CH₂Cl₂ / 16 h / 20 °C

With dmap; lithium hydroxide; 2,4,6-trichlorobenzoyl chloride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; 7.2: Yamaguchi coupling;
DOI:10.1016/j.tetlet.2004.04.164