Benzoic acid (1R,5S,6S)-5-fluoro-6-hydroxy-3-methoxycarbonyl-cyclohex-3-enyl ester

Base Information

• Chemical Name: Benzoic acid (1R,5S,6S)-5-fluoro-6-hydroxy-3-methoxycarbonyl-cyclohex-3-enyl ester
• CAS No.: 179914-52-4
• Molecular Formula: C₁₅H₁₅FO₅
• Molecular Weight: 294.28

Synonyms:Benzoic acid (1R,5S,6S)-5-fluoro-6-hydroxy-3-methoxycarbonyl-cyclohex-3-enyl ester

Chemical Property of Benzoic acid (1R,5S,6S)-5-fluoro-6-hydroxy-3-methoxycarbonyl-cyclohex-3-enyl ester

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Technology Process of Benzoic acid (1R,5S,6S)-5-fluoro-6-hydroxy-3-methoxycarbonyl-cyclohex-3-enyl ester

There total 3 articles about Benzoic acid (1R,5S,6S)-5-fluoro-6-hydroxy-3-methoxycarbonyl-cyclohex-3-enyl 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: 48.0%

(1R,5R,6S)-5-Benzoyloxy-7-oxa-bicyclo[4.1.0]hept-2-ene-3-carboxylic acid methyl ester (179738-34-2) → Benzoic acid (1R,5S,6R)-5,6-dihydroxy-3-methoxycarbonyl-cyclohex-3-enyl ester + Benzoic acid (1R,5S,6S)-5-fluoro-6-hydroxy-3-methoxycarbonyl-cyclohex-3-enyl ester (179914-52-4)

Guidance literature:

With pyridine; hydrogen fluoride; In dichloromethane; at 5 ℃; for 0.0833333h;

DOI:10.1016/0040-4020(96)00574-1

Reference yield: 8.0%

(1R,5R,6S)-5-Benzoyloxy-7-oxa-bicyclo[4.1.0]hept-2-ene-3-carboxylic acid methyl ester (179738-34-2) → Benzoic acid (1R,5S,6R)-5,6-dihydroxy-3-methoxycarbonyl-cyclohex-3-enyl ester + Benzoic acid (1R,5S,6S)-5-fluoro-6-hydroxy-3-methoxycarbonyl-cyclohex-3-enyl ester (179914-52-4) + Benzoic acid (1R,5R,6S)-5-fluoro-6-hydroxy-3-methoxycarbonyl-cyclohex-3-enyl ester

Guidance literature:

With pyridine; polyhydrogen fluoride; at 0 ℃; Title compound not separated from byproducts;

DOI:10.1016/0960-894X(96)00215-6

Reference yield:

Benzoic acid (1S,2S,6R)-2-bromo-6-hydroxy-4-methoxycarbonyl-cyclohex-3-enyl ester (179738-33-1) → Benzoic acid (1R,5S,6S)-5-fluoro-6-hydroxy-3-methoxycarbonyl-cyclohex-3-enyl ester (179914-52-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 62 percent / KCN / methanol / 3 h / Ambient temperature

2: 48 percent / HF, pyridine / CH₂Cl₂ / 0.08 h / 5 °C

With pyridine; potassium cyanide; hydrogen fluoride; In methanol; dichloromethane;

DOI:10.1016/0040-4020(96)00574-1

upstream raw materials:

(1R,5R,6S)-5-Benzoyloxy-7-oxa-bicyclo[4.1.0]hept-2-ene-3-carboxylic acid methyl ester

Benzoic acid (1S,2S,6R)-2-bromo-6-hydroxy-4-methoxycarbonyl-cyclohex-3-enyl ester

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