L-Valine, N-[(1,1-dimethylethoxy)carbonyl]-3-hydroxy-N-methyl-, (1R)-2-methyl-1-[(phenylmethoxy)carbonyl]propyl ester

Base Information

• Chemical Name: L-Valine, N-[(1,1-dimethylethoxy)carbonyl]-3-hydroxy-N-methyl-, (1R)-2-methyl-1-[(phenylmethoxy)carbonyl]propyl ester
• CAS No.: 872689-53-7
• Molecular Formula: C₂₃H₃₅NO₇
• Molecular Weight: 437.533
• Mol file: 872689-53-7.mol

Synonyms:

Chemical Property of L-Valine, N-[(1,1-dimethylethoxy)carbonyl]-3-hydroxy-N-methyl-, (1R)-2-methyl-1-[(phenylmethoxy)carbonyl]propyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of L-Valine, N-[(1,1-dimethylethoxy)carbonyl]-3-hydroxy-N-methyl-, (1R)-2-methyl-1-[(phenylmethoxy)carbonyl]propyl ester

There total 11 articles about L-Valine, N-[(1,1-dimethylethoxy)carbonyl]-3-hydroxy-N-methyl-, (1R)-2-methyl-1-[(phenylmethoxy)carbonyl]propyl 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) → (S)-2-(tert-Butoxycarbonyl-methyl-amino)-3-hydroxy-3-methyl-butyric acid (R)-1-benzyloxycarbonyl-2-methyl-propyl ester (872689-53-7)

Guidance literature:

Multi-step reaction with 5 steps

1: CDCl₃

2: 86 percent / sodium cyanoborohydride; HCl / dioxane / 1 h / 20 °C

3: 82 percent / hydrogen / palladium(II) hydroxide on carbon / tetrahydrofuran / 24 h / 20 °C / 3800 Torr

4: 87 percent / sodium phosphate buffer; sodium chlorite; sodium hypochlorite / TEMPO / H₂O; acetonitrile / 35 °C / pH 6.7

5: triphenylphosphine; diisopropyl azodicarboxylate / CH₂Cl₂; tetrahydrofuran / -20 - 20 °C

With hydrogenchloride; sodium hypochlorite; sodium chlorite; sodium phosphate buffer; di-isopropyl azodicarboxylate; hydrogen; sodium cyanoborohydride; triphenylphosphine; 2,2,6,6-tetramethyl-piperidine-N-oxyl; palladium dihydroxide; In tetrahydrofuran; 1,4-dioxane; chloroform-d1; dichloromethane; water; acetonitrile; 5: Mitsunobu reaction;

DOI:10.1139/v05-033

Reference yield:

(4R)-4-hydroxymethyl-5,5-dimethyl-3-(9-phenylfluoren-9-yl)oxazolidine (872689-49-1) → (S)-2-(tert-Butoxycarbonyl-methyl-amino)-3-hydroxy-3-methyl-butyric acid (R)-1-benzyloxycarbonyl-2-methyl-propyl ester (872689-53-7)

Guidance literature:

Multi-step reaction with 4 steps

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

2: 82 percent / hydrogen / palladium(II) hydroxide on carbon / tetrahydrofuran / 24 h / 20 °C / 3800 Torr

3: 87 percent / sodium phosphate buffer; sodium chlorite; sodium hypochlorite / TEMPO / H₂O; acetonitrile / 35 °C / pH 6.7

4: triphenylphosphine; diisopropyl azodicarboxylate / CH₂Cl₂; tetrahydrofuran / -20 - 20 °C

With hydrogenchloride; sodium hypochlorite; sodium chlorite; sodium phosphate buffer; di-isopropyl azodicarboxylate; hydrogen; sodium cyanoborohydride; triphenylphosphine; 2,2,6,6-tetramethyl-piperidine-N-oxyl; palladium dihydroxide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; acetonitrile; 4: Mitsunobu reaction;

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) → (S)-2-(tert-Butoxycarbonyl-methyl-amino)-3-hydroxy-3-methyl-butyric acid (R)-1-benzyloxycarbonyl-2-methyl-propyl ester (872689-53-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 82 percent / hydrogen / palladium(II) hydroxide on carbon / tetrahydrofuran / 24 h / 20 °C / 3800 Torr

2: 87 percent / sodium phosphate buffer; sodium chlorite; sodium hypochlorite / TEMPO / H₂O; acetonitrile / 35 °C / pH 6.7

3: triphenylphosphine; diisopropyl azodicarboxylate / CH₂Cl₂; tetrahydrofuran / -20 - 20 °C

With sodium hypochlorite; sodium chlorite; sodium phosphate buffer; di-isopropyl azodicarboxylate; hydrogen; triphenylphosphine; 2,2,6,6-tetramethyl-piperidine-N-oxyl; palladium dihydroxide; In tetrahydrofuran; dichloromethane; water; acetonitrile; 3: Mitsunobu reaction;

DOI:10.1139/v05-033

upstream raw materials:

(S)-2-hydroxy-3-methylbutyric acid benzyl ester

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

(S)-2-trimethylsilyloxy-3-methylbutyric acid trimethylsilyl ester

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