(S)-3-[(E)-5-(tert-butyl-dimethyl-silanyloxy)-4-methyl-pent-3-enyl]-5-((Z)-3-iodo-2-methyl-allyl)-3-phenylselanyl-dihydro-furan-2-one

Base Information

• Chemical Name: (S)-3-[(E)-5-(tert-butyl-dimethyl-silanyloxy)-4-methyl-pent-3-enyl]-5-((Z)-3-iodo-2-methyl-allyl)-3-phenylselanyl-dihydro-furan-2-one
• CAS No.: 912344-20-8
• Molecular Formula: C₂₆H₃₉IO₃SeSi
• Molecular Weight: 633.544
• Mol file: 912344-20-8.mol

Synonyms:(S)-3-[(E)-5-(tert-butyl-dimethyl-silanyloxy)-4-methyl-pent-3-enyl]-5-((Z)-3-iodo-2-methyl-allyl)-3-phenylselanyl-dihydro-furan-2-one

Chemical Property of (S)-3-[(E)-5-(tert-butyl-dimethyl-silanyloxy)-4-methyl-pent-3-enyl]-5-((Z)-3-iodo-2-methyl-allyl)-3-phenylselanyl-dihydro-furan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-3-[(E)-5-(tert-butyl-dimethyl-silanyloxy)-4-methyl-pent-3-enyl]-5-((Z)-3-iodo-2-methyl-allyl)-3-phenylselanyl-dihydro-furan-2-one

There total 10 articles about (S)-3-[(E)-5-(tert-butyl-dimethyl-silanyloxy)-4-methyl-pent-3-enyl]-5-((Z)-3-iodo-2-methyl-allyl)-3-phenylselanyl-dihydro-furan-2-one 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:

acetic acid (E)-6-(tert-butyl-dimethyl-silanyloxy)-1-((Z)-(S)-2-hydroxy-5-iodo-4-methyl-pent-4-enyl)-5-methyl-1-phenylselanyl-hex-4-enyl ester (912344-19-5) → (S)-3-[(E)-5-(tert-butyl-dimethyl-silanyloxy)-4-methyl-pent-3-enyl]-5-((Z)-3-iodo-2-methyl-allyl)-3-phenylselanyl-dihydro-furan-2-one (912344-20-8)

Guidance literature:

With toluene-4-sulfonic acid; In dichloromethane; at 20 ℃;

DOI:10.1016/j.tetlet.2006.06.150

Reference yield:

(S)-2-((Z)-3-iodo-2-methyl-allyl)-oxirane (912344-17-3) → (S)-3-[(E)-5-(tert-butyl-dimethyl-silanyloxy)-4-methyl-pent-3-enyl]-5-((Z)-3-iodo-2-methyl-allyl)-3-phenylselanyl-dihydro-furan-2-one (912344-20-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: NaHMDS / tetrahydrofuran / -78 °C

1.2: 60 percent / BF₃*OEt₃ / tetrahydrofuran / -78 - 20 °C

2.1: p-TSA / CH₂Cl₂ / 20 °C

With sodium hexamethyldisilazane; toluene-4-sulfonic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tetlet.2006.06.150

Reference yield:

(Z)-(S)-5-Iodo-4-methyl-pent-4-ene-1,2-diol (851760-67-3) → (S)-3-[(E)-5-(tert-butyl-dimethyl-silanyloxy)-4-methyl-pent-3-enyl]-5-((Z)-3-iodo-2-methyl-allyl)-3-phenylselanyl-dihydro-furan-2-one (912344-20-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: pyridine / 0 - 3 °C

2.1: 73 percent / K₂CO₃ / methanol

3.1: NaHMDS / tetrahydrofuran / -78 °C

3.2: 60 percent / BF₃*OEt₃ / tetrahydrofuran / -78 - 20 °C

4.1: p-TSA / CH₂Cl₂ / 20 °C

With pyridine; sodium hexamethyldisilazane; potassium carbonate; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1016/j.tetlet.2006.06.150

upstream raw materials:

acetic acid (E)-6-(tert-butyl-dimethyl-silanyloxy)-1-((Z)-(S)-2-hydroxy-5-iodo-4-methyl-pent-4-enyl)-5-methyl-1-phenylselanyl-hex-4-enyl ester

(S)-2-((Z)-3-iodo-2-methyl-allyl)-oxirane

(Z)-(S)-5-Iodo-4-methyl-pent-4-ene-1,2-diol

(E)-7-(tert-butyl-dimethyl-silanyloxy)-6-methyl-hept-5-enoic acid methyl ester