methyl 3,4,5-tri-O-acetyl-4-epi-shikimate

Base Information

• Chemical Name: methyl 3,4,5-tri-O-acetyl-4-epi-shikimate
• CAS No.: 104528-69-0
• Molecular Formula: C₁₄H₁₈O₈
• Molecular Weight: 314.292
• Mol file: 104528-69-0.mol

Synonyms:methyl 3,4,5-tri-O-acetyl-4-epi-shikimate

Chemical Property of methyl 3,4,5-tri-O-acetyl-4-epi-shikimate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 3,4,5-tri-O-acetyl-4-epi-shikimate

There total 20 articles about methyl 3,4,5-tri-O-acetyl-4-epi-shikimate 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:

(1S,4R,8S)-8-((S)-2-Methyl-1-phenyl-propoxy)-4-(toluene-4-sulfonyl)-2-oxa-bicyclo[2.2.2]oct-5-en-3-one (104464-04-2) → methyl 3,4,5-tri-O-acetyl-4-epi-shikimate (104528-69-0)

Guidance literature:

Multi-step reaction with 11 steps

1: 93 percent / methanol; CH₂Cl₂ / 0.08 h / -78 °C

2: 1.) aluminum amalgam; 2.) p-nitroperbenzoic acid / 1.) reflux; 2.) 0 deg C, chloroform, room temperature, 16 h

3: DBU / CH₂Cl₂ / -78 deg C, 5 min, room temperature, 2.5 h

4: hydrogen / 10percent Pd-C / ethanol / 12 h

5: trifluoroacetic acid / CH₂Cl₂ / 0 °C

6: p-toluenesulfonic acid / CH₂Cl₂ / 20 h / Ambient temperature

7: 1.) triethylamine, methanesulfonyl chloride; 2.) DBU / 1.) dichloromethane, 0 deg C, 3 h; 2.) dichloromethane, 0 deg C

8: 1.) lithium diisopropylamide; 2.) acetic acid / 1.) dichloromethane, THF, -100 deg C, 70 min; 2.) THF, -70 deg C, 20 min, room temperature

9: m-CPBA / CH₂Cl₂ / 48 h / 0 °C

10: DBU / CH₂Cl₂ / 18 h / 0 °C

11: 1.) p-toluenesulfonic acid; 2.) 4-(dimethylamino)pyridine, triethylamine / 1.) methanol, room temperature, 9 h; 2.) 0 deg C, dichloromethane, room temperature, 2 h

With 4-nitroperbenzoic acid; dmap; aluminium amalgam; hydrogen; toluene-4-sulfonic acid; acetic acid; methanesulfonyl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; lithium diisopropyl amide; palladium on activated charcoal; In methanol; ethanol; dichloromethane;

DOI:10.1021/ja00283a036

Reference yield:

(3R,4S,6S)-3,4-Dihydroxy-6-((S)-2-methyl-1-phenyl-propoxy)-cyclohex-1-enecarboxylic acid methyl ester (104464-08-6) → methyl 3,4,5-tri-O-acetyl-4-epi-shikimate (104528-69-0)

Guidance literature:

Multi-step reaction with 8 steps

1: hydrogen / 10percent Pd-C / ethanol / 12 h

2: trifluoroacetic acid / CH₂Cl₂ / 0 °C

3: p-toluenesulfonic acid / CH₂Cl₂ / 20 h / Ambient temperature

4: 1.) triethylamine, methanesulfonyl chloride; 2.) DBU / 1.) dichloromethane, 0 deg C, 3 h; 2.) dichloromethane, 0 deg C

5: 1.) lithium diisopropylamide; 2.) acetic acid / 1.) dichloromethane, THF, -100 deg C, 70 min; 2.) THF, -70 deg C, 20 min, room temperature

6: m-CPBA / CH₂Cl₂ / 48 h / 0 °C

7: DBU / CH₂Cl₂ / 18 h / 0 °C

8: 1.) p-toluenesulfonic acid; 2.) 4-(dimethylamino)pyridine, triethylamine / 1.) methanol, room temperature, 9 h; 2.) 0 deg C, dichloromethane, room temperature, 2 h

With dmap; hydrogen; toluene-4-sulfonic acid; acetic acid; methanesulfonyl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; lithium diisopropyl amide; palladium on activated charcoal; In ethanol; dichloromethane;

DOI:10.1021/ja00283a036

Reference yield:

(1R,3S,5S,6S)-5-Hydroxy-3-((S)-2-methyl-1-phenyl-propoxy)-7-oxa-bicyclo[4.1.0]heptane-2-carboxylic acid methyl ester → methyl 3,4,5-tri-O-acetyl-4-epi-shikimate (104528-69-0)

Guidance literature:

Multi-step reaction with 9 steps

1: DBU / CH₂Cl₂ / -78 deg C, 5 min, room temperature, 2.5 h

2: hydrogen / 10percent Pd-C / ethanol / 12 h

3: trifluoroacetic acid / CH₂Cl₂ / 0 °C

4: p-toluenesulfonic acid / CH₂Cl₂ / 20 h / Ambient temperature

5: 1.) triethylamine, methanesulfonyl chloride; 2.) DBU / 1.) dichloromethane, 0 deg C, 3 h; 2.) dichloromethane, 0 deg C

6: 1.) lithium diisopropylamide; 2.) acetic acid / 1.) dichloromethane, THF, -100 deg C, 70 min; 2.) THF, -70 deg C, 20 min, room temperature

7: m-CPBA / CH₂Cl₂ / 48 h / 0 °C

8: DBU / CH₂Cl₂ / 18 h / 0 °C

9: 1.) p-toluenesulfonic acid; 2.) 4-(dimethylamino)pyridine, triethylamine / 1.) methanol, room temperature, 9 h; 2.) 0 deg C, dichloromethane, room temperature, 2 h

With dmap; hydrogen; toluene-4-sulfonic acid; acetic acid; methanesulfonyl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; lithium diisopropyl amide; palladium on activated charcoal; In ethanol; dichloromethane;

DOI:10.1021/ja00283a036

upstream raw materials:

acetic anhydride

(3aR,7R,7aS)-methyl 7-hydroxy-2,2-dimethyl-3a,4,7,7atetrahydrobenzo[d][1,3]dioxole-5-carboxylate

(-)-methyl 4-epi-shikimate

(3R,4R,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid

Refernces

• 1、 Posner, Gary H.,Wettlaufer, David G.. "Highly Stereocontrolled Synyhesis of Some Trioxygenated Cyclohexenes: An Asymmetric Total Synthesis of (-)-Methyl Triacetyl-4-epishikimate". . p. 7373 - 7377. Retrieved 2007/10/02.