(2R,3R)-2-methyl-3-(((2S,3R)-2-((2E,4E)-4-methylhexa-2,4-dienamido)-3-phenylbutanoyl)oxy)butanoic acid

Base Information

• Chemical Name: (2R,3R)-2-methyl-3-(((2S,3R)-2-((2E,4E)-4-methylhexa-2,4-dienamido)-3-phenylbutanoyl)oxy)butanoic acid
• CAS No.: 1377321-85-1
• Molecular Formula: C₂₂H₂₉NO₅
• Molecular Weight: 387.476
• Mol file: 1377321-85-1.mol

Synonyms:(2R,3R)-2-methyl-3-(((2S,3R)-2-((2E,4E)-4-methylhexa-2,4-dienamido)-3-phenylbutanoyl)oxy)butanoic acid

Chemical Property of (2R,3R)-2-methyl-3-(((2S,3R)-2-((2E,4E)-4-methylhexa-2,4-dienamido)-3-phenylbutanoyl)oxy)butanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R)-2-methyl-3-(((2S,3R)-2-((2E,4E)-4-methylhexa-2,4-dienamido)-3-phenylbutanoyl)oxy)butanoic acid

There total 13 articles about (2R,3R)-2-methyl-3-(((2S,3R)-2-((2E,4E)-4-methylhexa-2,4-dienamido)-3-phenylbutanoyl)oxy)butanoic 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: 80.0%

C22H31NO4 → (2R,3R)-2-methyl-3-(((2S,3R)-2-((2E,4E)-4-methylhexa-2,4-dienamido)-3-phenylbutanoyl)oxy)butanoic acid (1377321-85-1)

Guidance literature:

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; In dichloromethane; water; at 0 - 20 ℃; for 5h; stereoselective reaction;

DOI:10.1055/s-0039-1691503

Reference yield:

(2E)-3-phenyl-2-propen-1-ol (4407-36-7) → (2R,3R)-2-methyl-3-(((2S,3R)-2-((2E,4E)-4-methylhexa-2,4-dienamido)-3-phenylbutanoyl)oxy)butanoic acid (1377321-85-1)

Guidance literature:

Multi-step reaction with 11 steps

1.1: titanium(IV) isopropylate / dichloromethane / 0.5 h / -20 °C / Molecular sieve

1.2: 16 h / -20 °C / Molecular sieve

2.1: copper(l) iodide / diethyl ether / 0.33 h / -40 °C

2.2: 20 °C

3.1: 1H-imidazole / dichloromethane / 0 - 35 °C

4.1: di-isopropyl azodicarboxylate / tetrahydrofuran / 0.08 h / 0 °C

4.2: 27 h / 20 - 35 °C

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 - 20 °C

6.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / dichloromethane; water / 4 h / 0 - 20 °C

7.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 2 h / 20 °C

7.2: 6 h / 20 °C

8.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 4 h / 20 °C / 760.05 Torr

9.1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate / N,N-dimethyl-formamide / 0.25 h / 0 °C

9.2: 6 h / 0 - 35 °C

10.1: pyridine hydrogenfluoride / acetonitrile / 12 h / 0 °C

11.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane; water / 5 h / 0 - 20 °C

With 1H-imidazole; titanium(IV) isopropylate; copper(l) iodide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; di-isopropyl azodicarboxylate; 2,4,6-trichlorobenzoyl chloride; palladium 10% on activated carbon; tetrabutyl ammonium fluoride; hydrogen; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; pyridine hydrogenfluoride; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; 1.1: |Sharpless Asymmetric Epoxidation / 1.2: |Sharpless Asymmetric Epoxidation / 4.1: |Mitsunobu Displacement / 4.2: |Mitsunobu Displacement;

DOI:10.1055/s-0039-1691503

Reference yield:

C31H41NO3Si → (2R,3R)-2-methyl-3-(((2S,3R)-2-((2E,4E)-4-methylhexa-2,4-dienamido)-3-phenylbutanoyl)oxy)butanoic acid (1377321-85-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate / N,N-dimethyl-formamide / 0.25 h / 0 °C

1.2: 6 h / 0 - 35 °C

2.1: pyridine hydrogenfluoride / acetonitrile / 12 h / 0 °C

3.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane; water / 5 h / 0 - 20 °C

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; pyridine hydrogenfluoride; In dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1055/s-0039-1691503

upstream raw materials:

(2E)-3-phenyl-2-propen-1-ol

(2S,3S)-2,3-epoxy-3-phenyl-1-propanol

(2R,3R)-3-phenyl-butane-1,2-diol

(2R,3R)-1-[(tert-butyldimethylsilyl)oxy]-3-phenyl-2-butanol

Downstream raw materials:

C₃₉H₄₀N₂O₄

C₃₁H₃₈N₂O₆

C₃₁H₃₈N₂O₆

C₃₂H₂₈F₃NO₄