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

Base Information

• Chemical Name: (3S,4S,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-3,4-dihydroxy-cyclohex-1-enecarboxylic acid tert-butyl ester
• CAS No.: 191795-31-0
• Molecular Formula: C₁₇H₃₂O₅Si
• Molecular Weight: 344.524
• Mol file: 191795-31-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 4 articles about (3S,4S,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-3,4-dihydroxy-cyclohex-1-enecarboxylic 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:

(S)-5-(tert-Butyl-dimethyl-silanyloxy)-cyclohexa-1,3-dienecarboxylic acid tert-butyl ester (191795-32-1) → (3S,4S,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-3,4-dihydroxy-cyclohex-1-enecarboxylic acid tert-butyl ester (191795-31-0)

Guidance literature:

With osmium(VIII) oxide; trimethylamine-N-oxide; In acetone; Yield given;

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

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → (3S,4S,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-3,4-dihydroxy-cyclohex-1-enecarboxylic acid tert-butyl ester (191795-31-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 2,6-futidine / CH₂Cl₂ / 0 °C

2: aq. OsO₄, Me₃NO / acetone

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

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

Reference yield:

(S)-5-Hydroxy-cyclohexa-1,3-dienecarboxylic acid tert-butyl ester (191795-30-9) → (3S,4S,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-3,4-dihydroxy-cyclohex-1-enecarboxylic acid tert-butyl ester (191795-31-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 2,6-futidine / CH₂Cl₂ / 0 °C

2: aq. OsO₄, Me₃NO / acetone

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

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

upstream raw materials:

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

t-butyldimethylsiyl triflate

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

Downstream raw materials:

(+)-shikimic acid