4-allyl 1-benzyl (2S)-2-hydroxybutanedioate

Base Information

• Chemical Name: 4-allyl 1-benzyl (2S)-2-hydroxybutanedioate
• CAS No.: 276870-98-5
• Molecular Formula: C₁₄H₁₆O₅
• Molecular Weight: 264.278
• Mol file: 276870-98-5.mol

Synonyms:4-allyl 1-benzyl (2S)-2-hydroxybutanedioate

Chemical Property of 4-allyl 1-benzyl (2S)-2-hydroxybutanedioate

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

Useful:

Technology Process of 4-allyl 1-benzyl (2S)-2-hydroxybutanedioate

There total 1 articles about 4-allyl 1-benzyl (2S)-2-hydroxybutanedioate 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: 92.0%

(S)-3-(Benzyloxycarbonyl)-3-hydroxypropanoic acid (66178-04-9) + allyl bromide (106-95-6) → 4-allyl 1-benzyl (2S)-2-hydroxybutanedioate (276870-98-5)

Guidance literature:

With tetrabutylammomium bromide; potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 4h;

DOI:10.1002/1099-0690(200004)2000:7<1207::AID-EJOC1207>3.0.CO;2-2

Reference yield:

4-allyl 1-benzyl (2S)-2-hydroxybutanedioate (276870-98-5) → (2S)-2-(tert-butyldiphenylsilyloxy)-4-[(1S)-1-carboxy-2-propoxycarbonylethoxy]-4-oxobutanoic acid

Guidance literature:

Multi-step reaction with 2 steps

1: 5.96 g / pyridine / CH₂Cl₂ / -78 - 20 °C

2: 23 percent / H₂ / 10percent Pd/C / dioxane / 4.5 h / 20 °C

With pyridine; hydrogen; 10percent Pd/C; In 1,4-dioxane; dichloromethane; 1: Substitution / 2: Hydrogenolysis;

DOI:10.1002/1099-0690(200004)2000:7<1207::AID-EJOC1207>3.0.CO;2-2

Reference yield:

4-allyl 1-benzyl (2S)-2-hydroxybutanedioate (276870-98-5) → (2S)-2-[(3S)-3-benzyloxycarbonyl-3-(tert-butyldiphenylsilyloxy)propanoyloxy]-3-(propoxycarbonyl)propanoic acid

Guidance literature:

Multi-step reaction with 2 steps

1: 5.96 g / pyridine / CH₂Cl₂ / -78 - 20 °C

2: 56 percent / H₂ / 10percent Pd/C / dioxane / 4.5 h / 20 °C

With pyridine; hydrogen; 10percent Pd/C; In 1,4-dioxane; dichloromethane; 1: Substitution / 2: Hydrogenolysis;

DOI:10.1002/1099-0690(200004)2000:7<1207::AID-EJOC1207>3.0.CO;2-2

upstream raw materials:

(S)-3-(Benzyloxycarbonyl)-3-hydroxypropanoic acid

allyl bromide

Downstream raw materials:

4-allyl 1-benzyl (2S)-2-[(3S)-3-benzyloxycarbonyl-3-(tert-butyldiphenylsilyloxy)propanoyloxy]butanedioate

4-allyl 1-benzyl (2S)-2-[(3S)-3-benzyloxycarbonyl-3-hydroxypropanoyloxy]butanedioate

(3S)-3-benzyloxycarbonyl-3-[(3S)-3-benzyloxycarbonyl-3-(tert-butyldiphenylsilyloxy)propanoyloxy]propanoic acid

(S)-2-Hydroxy-succinic acid 4-{(S)-2-[(S)-2-((S)-2-allyloxycarbonyl-1-benzyloxycarbonyl-ethoxycarbonyl)-1-benzyloxycarbonyl-ethoxycarbonyl]-1-benzyloxycarbonyl-ethyl} ester 1-benzyl ester