(S)-3-{5'-[(S)-2-((2S,3S)-2-Benzyloxycarbonylamino-3-methyl-pentanoylamino)-2-tert-butoxycarbonyl-ethyl]-2',3'-diisopropoxy-6-methoxy-biphenyl-3-yl}-2-tert-butoxycarbonylamino-propionic acid

Base Information

Chemical Name:(S)-3-{5'-[(S)-2-((2S,3S)-2-Benzyloxycarbonylamino-3-methyl-pentanoylamino)-2-tert-butoxycarbonyl-ethyl]-2',3'-diisopropoxy-6-methoxy-biphenyl-3-yl}-2-tert-butoxycarbonylamino-propionic acid
CAS No.:351442-34-7
Molecular Formula:C₄₈H₆₇N₃O₁₂
Molecular Weight:878.073
Hs Code.:

(S)-3-{5'-[(S)-2-((2S,3S)-2-Benzyloxycarbonylamino-3-methyl-pentanoylamino)-2-tert-butoxycarbonyl-ethyl]-2',3'-diisopropoxy-6-methoxy-biphenyl-3-yl}-2-tert-butoxycarbonylamino-propionic acid

Synonyms:(S)-3-{5'-[(S)-2-((2S,3S)-2-Benzyloxycarbonylamino-3-methyl-pentanoylamino)-2-tert-butoxycarbonyl-ethyl]-2',3'-diisopropoxy-6-methoxy-biphenyl-3-yl}-2-tert-butoxycarbonylamino-propionic acid

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Chemical Property of (S)-3-{5'-[(S)-2-((2S,3S)-2-Benzyloxycarbonylamino-3-methyl-pentanoylamino)-2-tert-butoxycarbonyl-ethyl]-2',3'-diisopropoxy-6-methoxy-biphenyl-3-yl}-2-tert-butoxycarbonylamino-propionic acid

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Technology Process of (S)-3-{5'-[(S)-2-((2S,3S)-2-Benzyloxycarbonylamino-3-methyl-pentanoylamino)-2-tert-butoxycarbonyl-ethyl]-2',3'-diisopropoxy-6-methoxy-biphenyl-3-yl}-2-tert-butoxycarbonylamino-propionic acid

There total 12 articles about (S)-3-{5'-[(S)-2-((2S,3S)-2-Benzyloxycarbonylamino-3-methyl-pentanoylamino)-2-tert-butoxycarbonyl-ethyl]-2',3'-diisopropoxy-6-methoxy-biphenyl-3-yl}-2-tert-butoxycarbonylamino-propionic acid 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:

: 16414-34-9
3-bromo-4,5-dihydroxybenzaldehyde

: 351442-34-7
(S)-3-{5'-[(S)-2-((2S,3S)-2-Benzyloxycarbonylamino-3-methyl-pentanoylamino)-2-tert-butoxycarbonyl-ethyl]-2',3'-diisopropoxy-6-methoxy-biphenyl-3-yl}-2-tert-butoxycarbonylamino-propionic acid

Guidance literature:: Multi-step reaction with 11 steps

1.1: 83 percent / K₂CO₃ / dimethylsulfoxide / 120 h / 55 °C

2.1: 91 percent / p-TsOH / benzene / 5 h / Heating

3.1: BuLi / tetrahydrofuran; hexane / 0.67 h / -78 °C

3.2: B(OMe)3 / tetrahydrofuran; hexane / 15 h / 20 °C

3.3: 67 percent / HCl / tetrahydrofuran; hexane; H₂O / 2 h

4.1: Na₂CO₃ / Pd(PPh₃)4 / 1,2-dimethoxy-ethane; H₂O / 0.08 h / 20 °C

4.2: 85 percent / 1,2-dimethoxy-ethane; H₂O / 16 h / 95 °C

5.1: 80 percent / NaBH₄ / tetrahydrofuran / 1 h / -78 °C

6.1: triethylamine / CH₂Cl₂ / 2 h / 20 °C

7.1: 2.0 g / LiBr / acetone; CH₂Cl₂ / 16 h / 20 °C

8.1: CsOH*H₂O; N-methyl antracene-O-allyl cinchonidinium bromide / CH₂Cl₂ / 20 h / -50 °C

9.1: 294.0 mg / citric acid; silica gel / H₂O; tetrahydrofuran / 2 h

10.1: 90 percent / EDC; HOBt / CH₂Cl₂ / 15 h / 20 °C

11.1: 100 percent / LiOH / tetrahydrofuran; H₂O / 5 h / 20 °C / Saponification

With cesium hydroxide; lithium hydroxide; sodium tetrahydroborate; n-butyllithium; N-methyl antracene-O-allyl cinchonidinium bromide; silica gel; sodium carbonate; potassium carbonate; benzotriazol-1-ol; toluene-4-sulfonic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; citric acid; lithium bromide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,2-dimethoxyethane; hexane; dichloromethane; water; dimethyl sulfoxide; acetone; benzene; 4.1: Suzuki cross-coupling reaction / 7.1: Finkelstein bromination reaction;
DOI:10.1021/ol016021v

Reference yield:

: 2973-76-4
5-bromo-4-hydroxy-3-methoxybenzaldehyde

: 351442-34-7
(S)-3-{5'-[(S)-2-((2S,3S)-2-Benzyloxycarbonylamino-3-methyl-pentanoylamino)-2-tert-butoxycarbonyl-ethyl]-2',3'-diisopropoxy-6-methoxy-biphenyl-3-yl}-2-tert-butoxycarbonylamino-propionic acid

Guidance literature:: Multi-step reaction with 12 steps

1.1: 98 percent / AlCl₃; pyridine / CH₂Cl₂ / 24 h / 40 °C

2.1: 83 percent / K₂CO₃ / dimethylsulfoxide / 120 h / 55 °C

3.1: 91 percent / p-TsOH / benzene / 5 h / Heating

4.1: BuLi / tetrahydrofuran; hexane / 0.67 h / -78 °C

4.2: B(OMe)3 / tetrahydrofuran; hexane / 15 h / 20 °C

4.3: 67 percent / HCl / tetrahydrofuran; hexane; H₂O / 2 h

5.1: Na₂CO₃ / Pd(PPh₃)4 / 1,2-dimethoxy-ethane; H₂O / 0.08 h / 20 °C

5.2: 85 percent / 1,2-dimethoxy-ethane; H₂O / 16 h / 95 °C

6.1: 80 percent / NaBH₄ / tetrahydrofuran / 1 h / -78 °C

7.1: triethylamine / CH₂Cl₂ / 2 h / 20 °C

8.1: 2.0 g / LiBr / acetone; CH₂Cl₂ / 16 h / 20 °C

9.1: CsOH*H₂O; N-methyl antracene-O-allyl cinchonidinium bromide / CH₂Cl₂ / 20 h / -50 °C

10.1: 294.0 mg / citric acid; silica gel / H₂O; tetrahydrofuran / 2 h

11.1: 90 percent / EDC; HOBt / CH₂Cl₂ / 15 h / 20 °C

12.1: 100 percent / LiOH / tetrahydrofuran; H₂O / 5 h / 20 °C / Saponification

With pyridine; cesium hydroxide; lithium hydroxide; sodium tetrahydroborate; n-butyllithium; aluminium trichloride; N-methyl antracene-O-allyl cinchonidinium bromide; silica gel; sodium carbonate; potassium carbonate; benzotriazol-1-ol; toluene-4-sulfonic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; citric acid; lithium bromide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,2-dimethoxyethane; hexane; dichloromethane; water; dimethyl sulfoxide; acetone; benzene; 5.1: Suzuki cross-coupling reaction / 8.1: Finkelstein bromination reaction;
DOI:10.1021/ol016021v

Reference yield:

: 121-33-5,8014-42-4
vanillin

: 351442-34-7
(S)-3-{5'-[(S)-2-((2S,3S)-2-Benzyloxycarbonylamino-3-methyl-pentanoylamino)-2-tert-butoxycarbonyl-ethyl]-2',3'-diisopropoxy-6-methoxy-biphenyl-3-yl}-2-tert-butoxycarbonylamino-propionic acid

Guidance literature:: Multi-step reaction with 13 steps

1.1: 90 percent / Br₂ / acetic acid / 3 h / 20 °C

2.1: 98 percent / AlCl₃; pyridine / CH₂Cl₂ / 24 h / 40 °C

3.1: 83 percent / K₂CO₃ / dimethylsulfoxide / 120 h / 55 °C

4.1: 91 percent / p-TsOH / benzene / 5 h / Heating

5.1: BuLi / tetrahydrofuran; hexane / 0.67 h / -78 °C

5.2: B(OMe)3 / tetrahydrofuran; hexane / 15 h / 20 °C

5.3: 67 percent / HCl / tetrahydrofuran; hexane; H₂O / 2 h

6.1: Na₂CO₃ / Pd(PPh₃)4 / 1,2-dimethoxy-ethane; H₂O / 0.08 h / 20 °C

6.2: 85 percent / 1,2-dimethoxy-ethane; H₂O / 16 h / 95 °C

7.1: 80 percent / NaBH₄ / tetrahydrofuran / 1 h / -78 °C

8.1: triethylamine / CH₂Cl₂ / 2 h / 20 °C

9.1: 2.0 g / LiBr / acetone; CH₂Cl₂ / 16 h / 20 °C

10.1: CsOH*H₂O; N-methyl antracene-O-allyl cinchonidinium bromide / CH₂Cl₂ / 20 h / -50 °C

11.1: 294.0 mg / citric acid; silica gel / H₂O; tetrahydrofuran / 2 h

12.1: 90 percent / EDC; HOBt / CH₂Cl₂ / 15 h / 20 °C

13.1: 100 percent / LiOH / tetrahydrofuran; H₂O / 5 h / 20 °C / Saponification

With pyridine; cesium hydroxide; lithium hydroxide; sodium tetrahydroborate; n-butyllithium; aluminium trichloride; N-methyl antracene-O-allyl cinchonidinium bromide; bromine; silica gel; sodium carbonate; potassium carbonate; benzotriazol-1-ol; toluene-4-sulfonic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; citric acid; lithium bromide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,2-dimethoxyethane; hexane; dichloromethane; water; acetic acid; dimethyl sulfoxide; acetone; benzene; 6.1: Suzuki cross-coupling reaction / 9.1: Finkelstein bromination reaction;
DOI:10.1021/ol016021v