(S)-5-Hydroxy-cyclohexa-1,3-dienecarboxylic acid tert-butyl ester

Base Information

• Chemical Name: (S)-5-Hydroxy-cyclohexa-1,3-dienecarboxylic acid tert-butyl ester
• CAS No.: 191795-30-9
• Molecular Formula: C₁₁H₁₆O₃
• Molecular Weight: 196.246
• Mol file: 191795-30-9.mol

Synonyms:(S)-5-Hydroxy-cyclohexa-1,3-dienecarboxylic acid tert-butyl ester

Chemical Property of (S)-5-Hydroxy-cyclohexa-1,3-dienecarboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-5-Hydroxy-cyclohexa-1,3-dienecarboxylic acid tert-butyl ester

There total 1 articles about (S)-5-Hydroxy-cyclohexa-1,3-dienecarboxylic acid tert-butyl 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: 94.0%

7-Oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid tert-butyl ester → (S)-5-Hydroxy-cyclohexa-1,3-dienecarboxylic acid tert-butyl ester (191795-30-9)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 - 20 ℃;

DOI:10.1016/S0957-4166(97)00151-1

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) + (S)-5-Hydroxy-cyclohexa-1,3-dienecarboxylic acid tert-butyl ester (191795-30-9) → (S)-5-(tert-Butyl-dimethyl-silanyloxy)-cyclohexa-1,3-dienecarboxylic acid tert-butyl ester (191795-32-1)

Guidance literature:

With 2,6-futidine; In dichloromethane; at 0 ℃;

DOI:10.1016/S0957-4166(97)00151-1

Reference yield:

(S)-5-Hydroxy-cyclohexa-1,3-dienecarboxylic acid tert-butyl ester (191795-30-9) → (+)-shikimic acid (10191-00-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 2,6-futidine / CH₂Cl₂ / 0 °C

2: aq. OsO₄, Me₃NO / acetone

3: 100 percent / TFA / CH₂Cl₂ / 0.25 h / Ambient temperature

With osmium(VIII) oxide; trimethylamine-N-oxide; 2,6-futidine; trifluoroacetic acid; In dichloromethane; acetone;

DOI:10.1016/S0957-4166(97)00151-1

Downstream raw materials:

(S)-5-(tert-Butyl-dimethyl-silanyloxy)-cyclohexa-1,3-dienecarboxylic acid tert-butyl ester

(+)-shikimic acid

(3S,4S,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-3,4-dihydroxy-cyclohex-1-enecarboxylic acid tert-butyl ester