L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-3-hydroxy-N-methyl-L-valyl-, methyl ester

Base Information

• Chemical Name: L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-3-hydroxy-N-methyl-L-valyl-, methyl ester
• CAS No.: 872689-58-2
• Molecular Formula: C₂₁H₃₂N₂O₆
• Molecular Weight: 408.495
• Mol file: 872689-58-2.mol

Synonyms:

Chemical Property of L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-3-hydroxy-N-methyl-L-valyl-, methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-3-hydroxy-N-methyl-L-valyl-, methyl ester

There total 6 articles about L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-3-hydroxy-N-methyl-L-valyl-, methyl 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:

(4R)-4-(1-hydroxy-1-methylethyl)-3-(9-phenylfluoren-9-yl)oxazolidine (872689-48-0) → N-[(S)-β-hydroxy-N-(tert-butyloxycarbonyl)-N-methylvalinyl]-(S)-phenylalanine methyl ester (872689-58-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: CDCl₃

2.1: 86 percent / sodium cyanoborohydride; HCl / dioxane / 1 h / 20 °C

3.1: 82 percent / hydrogen / palladium(II) hydroxide on carbon / tetrahydrofuran / 24 h / 20 °C / 3800 Torr

4.1: 87 percent / sodium phosphate buffer; sodium chlorite; sodium hypochlorite / TEMPO / H₂O; acetonitrile / 35 °C / pH 6.7

5.1: TBTU; 1-hydroxybenzotriazole / acetonitrile / 0.5 h / 0 °C

5.2: diisopropylethylamine / acetonitrile / 48 h / 20 °C

With hydrogenchloride; sodium hypochlorite; sodium chlorite; sodium phosphate buffer; hydrogen; sodium cyanoborohydride; benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; 2,2,6,6-tetramethyl-piperidine-N-oxyl; palladium dihydroxide; In tetrahydrofuran; 1,4-dioxane; chloroform-d1; water; acetonitrile;

DOI:10.1139/v05-033

Reference yield:

(4R)-4-hydroxymethyl-5,5-dimethyl-3-(9-phenylfluoren-9-yl)oxazolidine (872689-49-1) → N-[(S)-β-hydroxy-N-(tert-butyloxycarbonyl)-N-methylvalinyl]-(S)-phenylalanine methyl ester (872689-58-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 86 percent / sodium cyanoborohydride; HCl / dioxane / 1 h / 20 °C

2.1: 82 percent / hydrogen / palladium(II) hydroxide on carbon / tetrahydrofuran / 24 h / 20 °C / 3800 Torr

3.1: 87 percent / sodium phosphate buffer; sodium chlorite; sodium hypochlorite / TEMPO / H₂O; acetonitrile / 35 °C / pH 6.7

4.1: TBTU; 1-hydroxybenzotriazole / acetonitrile / 0.5 h / 0 °C

4.2: diisopropylethylamine / acetonitrile / 48 h / 20 °C

With hydrogenchloride; sodium hypochlorite; sodium chlorite; sodium phosphate buffer; hydrogen; sodium cyanoborohydride; benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; 2,2,6,6-tetramethyl-piperidine-N-oxyl; palladium dihydroxide; In tetrahydrofuran; 1,4-dioxane; water; acetonitrile;

DOI:10.1139/v05-033

Reference yield:

(2R)-2-[N-methyl-N-(9-phenylfluoren-9-yl)]amino-3-methyl-1,3-butanediol (872689-51-5) → N-[(S)-β-hydroxy-N-(tert-butyloxycarbonyl)-N-methylvalinyl]-(S)-phenylalanine methyl ester (872689-58-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 82 percent / hydrogen / palladium(II) hydroxide on carbon / tetrahydrofuran / 24 h / 20 °C / 3800 Torr

2.1: 87 percent / sodium phosphate buffer; sodium chlorite; sodium hypochlorite / TEMPO / H₂O; acetonitrile / 35 °C / pH 6.7

3.1: TBTU; 1-hydroxybenzotriazole / acetonitrile / 0.5 h / 0 °C

3.2: diisopropylethylamine / acetonitrile / 48 h / 20 °C

With sodium hypochlorite; sodium chlorite; sodium phosphate buffer; hydrogen; benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; 2,2,6,6-tetramethyl-piperidine-N-oxyl; palladium dihydroxide; In tetrahydrofuran; water; acetonitrile;

DOI:10.1139/v05-033

upstream raw materials:

methyl (2S)-2-amino-3-phenylpropanoate hydrochloride

(S)-β-hydroxy-N-(tert-butyloxycarbonyl)-N-methylvaline

(4R)-4-(1-hydroxy-1-methylethyl)-3-(9-phenylfluoren-9-yl)oxazolidine

(4R)-4-hydroxymethyl-5,5-dimethyl-3-(9-phenylfluoren-9-yl)oxazolidine