(-)-methyl 4-epi-quinate

Base Information

• Chemical Name: (-)-methyl 4-epi-quinate
• CAS No.: 50459-25-1
• Molecular Formula: C₈H₁₄O₆
• Molecular Weight: 206.196
• Mol file: 50459-25-1.mol

Synonyms:(-)-methyl 4-epi-quinate

Chemical Property of (-)-methyl 4-epi-quinate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-methyl 4-epi-quinate

There total 7 articles about (-)-methyl 4-epi-quinate 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:

methyl quinicate (135711-62-5) → (-)-methyl 4-epi-quinate (50459-25-1)

Guidance literature:

Multi-step reaction with 4 steps

1: Dess-Martin periodane / dichloromethane / 20 °C

2: sodium tetrahydroborate / ethanol / 0.67 h / -30 °C

3: hydrogenchloride / water / 1 h

4: Amberlite IR₁₂₀ acidic resin / 12 h

With hydrogenchloride; sodium tetrahydroborate; Dess-Martin periodane; In ethanol; dichloromethane; water;

DOI:10.1021/acs.jafc.6b02472

Reference yield:

D-(-)-quinic acid (77-95-2) → (-)-methyl 4-epi-quinate (50459-25-1)

Guidance literature:

Multi-step reaction with 6 steps

1: Amberlite IR₁₂₀ acidic resin / 12 h / Reflux

2: triethylamine / N,N-dimethyl-formamide / 18 h / 0 - 20 °C / Inert atmosphere

3: Dess-Martin periodane / dichloromethane / 20 °C

4: sodium tetrahydroborate / ethanol / 0.67 h / -30 °C

5: hydrogenchloride / water / 1 h

6: Amberlite IR₁₂₀ acidic resin / 12 h

With hydrogenchloride; sodium tetrahydroborate; Dess-Martin periodane; triethylamine; In ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/acs.jafc.6b02472

Reference yield:

methyl (3R,5R)-1,4-dihydroxy-3,5-tert-butyldimethylsilyloxyclohexanecarboxylate → (-)-methyl 4-epi-quinate (50459-25-1)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogenchloride / water / 1 h

2: Amberlite IR₁₂₀ acidic resin / 12 h

With hydrogenchloride; In water;

DOI:10.1021/acs.jafc.6b02472

upstream raw materials:

D-(-)-quinic acid

methyl (-)-quinate

methanol

(1R,3R,4R,5R)-(-)-quinic acid

Downstream raw materials:

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