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

Base Information

• Chemical Name: 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
• CAS No.: 912344-19-5
• Molecular Formula: C₂₇H₄₃IO₄SeSi
• Molecular Weight: 665.586
• Mol file: 912344-19-5.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 8 articles about 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 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: 72.0%

(S)-2-((Z)-3-iodo-2-methyl-allyl)-oxirane (912344-17-3) + MeO2CCH(SePh)CH2CH2CH=C(Me)CH2OTBS (912344-18-4) → 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)

Guidance literature:

MeO₂CCH(SePh)CH₂CH₂CH=C(Me)CH₂OTBS; With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.583333h; Inert atmosphere;

(S)-2-((Z)-3-iodo-2-methyl-allyl)-oxirane; With boron trifluoride diethyl etherate; In tetrahydrofuran; at -78 - 20 ℃; Inert atmosphere;

DOI:10.1039/b910572g

Reference yield:

(Z)-(S)-5-Iodo-4-methyl-pent-4-ene-1,2-diol (851760-67-3) → 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)

Guidance literature:

Multi-step reaction with 3 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

With pyridine; sodium hexamethyldisilazane; potassium carbonate; In tetrahydrofuran; methanol;

DOI:10.1016/j.tetlet.2006.06.150

Reference yield:

(E)-7-(tert-butyl-dimethyl-silanyloxy)-6-methyl-hept-5-enoic acid methyl ester (912344-16-2) → 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)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 97 percent / LDA; TMSCl / tetrahydrofuran / -78 - 20 °C

2.1: NaHMDS / tetrahydrofuran / -78 °C

2.2: 60 percent / BF₃*OEt₃ / tetrahydrofuran / -78 - 20 °C

With chloro-trimethyl-silane; sodium hexamethyldisilazane; lithium diisopropyl amide; In tetrahydrofuran;

DOI:10.1016/j.tetlet.2006.06.150

upstream raw materials:

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

MeO₂CCH(SePh)CH₂CH₂CH=C(Me)CH₂OTBS

(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

Downstream raw materials:

(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