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

Base Information

• Chemical Name: (S)-5-(tert-Butyl-dimethyl-silanyloxy)-cyclohexa-1,3-dienecarboxylic acid methyl ester
• CAS No.: 186767-26-0
• Molecular Formula: C₁₄H₂₄O₃Si
• Molecular Weight: 268.428
• Mol file: 186767-26-0.mol

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

Chemical Property of (S)-5-(tert-Butyl-dimethyl-silanyloxy)-cyclohexa-1,3-dienecarboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-5-(tert-Butyl-dimethyl-silanyloxy)-cyclohexa-1,3-dienecarboxylic acid methyl ester

There total 3 articles about (S)-5-(tert-Butyl-dimethyl-silanyloxy)-cyclohexa-1,3-dienecarboxylic acid methyl 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: 90.0%

t-butyldimethylsiyl triflate (69739-34-0) + (1S,2S,4S)-7-Oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester (186766-46-1,204988-60-3) → (S)-5-(tert-Butyl-dimethyl-silanyloxy)-cyclohexa-1,3-dienecarboxylic acid methyl ester (186767-26-0)

Guidance literature:

With 2,6-dimethylpyridine; lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃;

DOI:10.1016/S0040-4039(96)02259-9

Reference yield:

(1S,2S,4S)-7-Oxa-bicyclo[2.2.1]hept-5-ene-2-carbothioic acid S-ethyl ester (245680-45-9) → (S)-5-(tert-Butyl-dimethyl-silanyloxy)-cyclohexa-1,3-dienecarboxylic acid methyl ester (186767-26-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 93 percent / Cs₂CO₃ / 0 °C

2.1: LiHMDS / tetrahydrofuran / -78 - 0 °C

2.2: 90 percent / 2,6-lutidine / tetrahydrofuran / -78 °C

With caesium carbonate; lithium hexamethyldisilazane; In tetrahydrofuran; 1.1: transesterification / 2.1: Ring cleavage / 2.2: silylation;

DOI:10.1021/ja991191c

Reference yield:

3-((1S,2S,4S)-7-Oxa-bicyclo[2.2.1]hept-5-ene-2-carbonyl)-oxazolidin-2-one (186666-50-2) → (S)-5-(tert-Butyl-dimethyl-silanyloxy)-cyclohexa-1,3-dienecarboxylic acid methyl ester (186767-26-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: tetrahydrofuran / -20 °C

2.1: 93 percent / Cs₂CO₃ / 0 °C

3.1: LiHMDS / tetrahydrofuran / -78 - 0 °C

3.2: 90 percent / 2,6-lutidine / tetrahydrofuran / -78 °C

With caesium carbonate; lithium hexamethyldisilazane; In tetrahydrofuran; 1.1: transesterification / 2.1: transesterification / 3.1: Ring cleavage / 3.2: silylation;

DOI:10.1021/ja991191c

upstream raw materials:

t-butyldimethylsiyl triflate

(1S,2S,4S)-7-Oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester

(1S,2S,4S)-7-Oxa-bicyclo[2.2.1]hept-5-ene-2-carbothioic acid S-ethyl ester

3-((1S,2S,4S)-7-Oxa-bicyclo[2.2.1]hept-5-ene-2-carbonyl)-oxazolidin-2-one

Downstream raw materials:

(+)-shikimic acid

(+)-Methyl shikimate

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