Benzyl 1-epi-3-dehydroquinate

Base Information

• Chemical Name: Benzyl 1-epi-3-dehydroquinate
• CAS No.: 155270-79-4
• Molecular Formula: C₁₄H₁₆O₆
• Molecular Weight: 280.277
• Mol file: 155270-79-4.mol

Synonyms:Benzyl 1-epi-3-dehydroquinate

Chemical Property of Benzyl 1-epi-3-dehydroquinate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzyl 1-epi-3-dehydroquinate

There total 6 articles about Benzyl 1-epi-3-dehydroquinate 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: 99.0%

Phenylmethyl <1S-(1α,3α,4β)>-3,4-bis<(tert-butyldimethylsilyl)oxy>-1-hydroxy-5-oxo-1-cyclohexanecarboxylate (155270-78-3) → Benzyl 1-epi-3-dehydroquinate (155270-79-4)

Guidance literature:

With hydrogen fluoride; In acetonitrile; at 0 ℃; for 0.0833333h;

DOI:10.1021/jo00087a024

Reference yield:

(1S,3R,4S,5R)-1,3,4-Triacetoxy-6-oxabicyclo<3.2.1>octan-7-one → Benzyl 1-epi-3-dehydroquinate (155270-79-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 34 percent / K₂CO₃ / methanol / 3 h / 21 °C

2: 36 percent / imidazole / dimethylformamide / 12 h / 21 °C

3: 81 percent / K₂CO₃ / 16 h / 21 °C

4: 53 percent / DMSO, oxalyl chloride / CH₂Cl₂ / 0.5 h / -78 °C

5: 99 percent / HF / acetonitrile / 0.08 h / 0 °C

With 1H-imidazole; oxalyl dichloride; hydrogen fluoride; potassium carbonate; dimethyl sulfoxide; In methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo00087a024

Reference yield:

(1R,3R,4R,5R)-3,4-Bis<(tert-butyldimethylsilyl)oxy>-1-hydroxy-6-oxabicyclo<3.2.1>octan-7-one (155270-76-1) → Benzyl 1-epi-3-dehydroquinate (155270-79-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 81 percent / K₂CO₃ / 16 h / 21 °C

2: 53 percent / DMSO, oxalyl chloride / CH₂Cl₂ / 0.5 h / -78 °C

3: 99 percent / HF / acetonitrile / 0.08 h / 0 °C

With oxalyl dichloride; hydrogen fluoride; potassium carbonate; dimethyl sulfoxide; In dichloromethane; acetonitrile;

DOI:10.1021/jo00087a024

upstream raw materials:

Phenylmethyl <1S-(1α,3α,4β)>-3,4-bis<(tert-butyldimethylsilyl)oxy>-1-hydroxy-5-oxo-1-cyclohexanecarboxylate

(1R,3R,4R,5R)-3,4-Bis<(tert-butyldimethylsilyl)oxy>-1-hydroxy-6-oxabicyclo<3.2.1>octan-7-one

Phenylmethyl <1S-(1α,3β,4β,5α)>-4,5-bis<(tert-butyldimethylsilyl)oxy>-1,3-dihydroxy-1-cyclohexanecarboxylate

(1S,3R,4S,5R)-1,3,4-trihydroxycyclohexane-1,5-carbolactone