(3S,4R)-4-Hydroxy-5-oxo-3-phenyl-tetrahydro-furan-3-carboxylic acid ethyl ester

Base Information

• Chemical Name: (3S,4R)-4-Hydroxy-5-oxo-3-phenyl-tetrahydro-furan-3-carboxylic acid ethyl ester
• CAS No.: 170450-62-1
• Molecular Formula: C₁₃H₁₄O₅
• Molecular Weight: 250.251

Synonyms:(3S,4R)-4-Hydroxy-5-oxo-3-phenyl-tetrahydro-furan-3-carboxylic acid ethyl ester

Chemical Property of (3S,4R)-4-Hydroxy-5-oxo-3-phenyl-tetrahydro-furan-3-carboxylic acid ethyl ester

Chemical Property:

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Technology Process of (3S,4R)-4-Hydroxy-5-oxo-3-phenyl-tetrahydro-furan-3-carboxylic acid ethyl ester

There total 1 articles about (3S,4R)-4-Hydroxy-5-oxo-3-phenyl-tetrahydro-furan-3-carboxylic acid ethyl 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: 44.0%

4,5-Dioxo-3-phenyl-tetrahydro-furan-3-carboxylic acid ethyl ester (170450-61-0) → (3R,4R)-4-Hydroxy-5-oxo-3-phenyl-tetrahydro-furan-3-carboxylic acid ethyl ester (170555-65-4) + (3S,4R)-4-Hydroxy-5-oxo-3-phenyl-tetrahydro-furan-3-carboxylic acid ethyl ester (170450-62-1)

Guidance literature:

With D-glucose; bakers' yeast; In ethanol; at 23 ℃; for 16h;

DOI:10.1021/jo00122a064

Reference yield: 76.0%

(3S,4R)-4-Hydroxy-5-oxo-3-phenyl-tetrahydro-furan-3-carboxylic acid ethyl ester (170450-62-1) → (3S,4R)-4-Hydroxy-3-hydroxymethyl-3-phenyl-dihydro-furan-2-one + (3S,4R)-4,5-Dihydroxy-3-phenyl-tetrahydro-furan-3-carboxylic acid ethyl ester

Guidance literature:

With lithium borohydride; In tetrahydrofuran; at 5 - 10 ℃;

DOI:10.1021/jo00122a064

Reference yield:

(3S,4R)-4-Hydroxy-5-oxo-3-phenyl-tetrahydro-furan-3-carboxylic acid ethyl ester (170450-62-1) → (S)-Diethyl 2-phenyl-2-(hydroxymethyl)glutarate (170450-69-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 76 percent / LiBH₄ / tetrahydrofuran / 5 - 10 °C

2: 73 percent / H₅IO₆ / tetrahydrofuran / 0.17 h

3: 75 percent / CHCl₃ / 1 h / Ambient temperature

4: H₂ / 5percent Pd/C / ethanol

5: HCl / ethanol

With hydrogenchloride; lithium borohydride; hydrogen; periodic acid; palladium on activated charcoal; In tetrahydrofuran; ethanol; chloroform;

DOI:10.1021/jo00122a064

upstream raw materials:

4,5-Dioxo-3-phenyl-tetrahydro-furan-3-carboxylic acid ethyl ester

Downstream raw materials:

(+)₄₀₄-3-(4-aminophenyl)-3-ethyl-2,6-piperidinedione

(R)-2-Phenyl-2-ethylglutaric acid

(R)-(+)-3-ethyl-3-(4-nitrophenyl)piperidine-2,6-dione

(R)-Diethyl 2-phenyl-2-vinylglutarate

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