(1E,3R,4R,5E)-1-iodo-2,4,6-trimethyl-3-(triphenylsiloxy)-7-bromo-1,5-heptadiene

Base Information

• Chemical Name: (1E,3R,4R,5E)-1-iodo-2,4,6-trimethyl-3-(triphenylsiloxy)-7-bromo-1,5-heptadiene
• CAS No.: 637741-03-8
• Molecular Formula: C₂₈H₃₀BrIOSi
• Molecular Weight: 617.44

Synonyms:(1E,3R,4R,5E)-1-iodo-2,4,6-trimethyl-3-(triphenylsiloxy)-7-bromo-1,5-heptadiene

Chemical Property of (1E,3R,4R,5E)-1-iodo-2,4,6-trimethyl-3-(triphenylsiloxy)-7-bromo-1,5-heptadiene

Chemical Property:

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Technology Process of (1E,3R,4R,5E)-1-iodo-2,4,6-trimethyl-3-(triphenylsiloxy)-7-bromo-1,5-heptadiene

There total 2 articles about (1E,3R,4R,5E)-1-iodo-2,4,6-trimethyl-3-(triphenylsiloxy)-7-bromo-1,5-heptadiene 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: 98.0%

(2E,4R,5R,6E)-2,4,6-trimethyl-5-(triphenylsiloxy)-7-iodo-2,6-heptadien-1-ol (361525-04-4) → (1E,3R,4R,5E)-1-iodo-2,4,6-trimethyl-3-(triphenylsiloxy)-7-bromo-1,5-heptadiene (637741-03-8)

Guidance literature:

With carbon tetrabromide; triphenylphosphine; In tetrahydrofuran; at 0 ℃; for 0.166667h;

DOI:10.1039/b305818b

Reference yield:

(2E,6E)-(4R,5R)-7-Iodo-2,4,6-trimethyl-5-triphenylsilanyloxy-hepta-2,6-dienoic acid ethyl ester (361525-03-3) → (1E,3R,4R,5E)-1-iodo-2,4,6-trimethyl-3-(triphenylsiloxy)-7-bromo-1,5-heptadiene (637741-03-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent / diisobutylaluminum hydride / CH₂Cl₂; hexane / 0.5 h / -78 °C

2: 98 percent / tetrabromomethane; triphenylphosphine / tetrahydrofuran / 0.17 h / 0 °C

With carbon tetrabromide; diisobutylaluminium hydride; triphenylphosphine; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1039/b305818b

Reference yield: 41.0%

(2R,3R,4R)-5-(tert-Butyl-dimethyl-silanyloxy)-1,3,4-tris-(4-methoxy-benzyloxy)-pentan-2-ol (331626-81-4) + (1E,3R,4R,5E)-1-iodo-2,4,6-trimethyl-3-(triphenylsiloxy)-7-bromo-1,5-heptadiene (637741-03-8) → (1E,3R,4R,5E,9R,10R,11R)-1-iodo-2,4,6-trimethyl-3-(triphenylsiloxy)-9-[(4-methoxybenzyloxy)methyl]-10,11-bis(4-methoxybenzyloxy)-12-(tert-butyldimethyl-siloxy)-8-oxa-1,5-dodecadiene (637741-04-9)

Guidance literature:

With 2,6-dibutylpyridine; silver trifluoromethanesulfonate; In dichloromethane; at 0 ℃; for 0.5h;

DOI:10.1039/b305818b

upstream raw materials:

(2E,4R,5R,6E)-2,4,6-trimethyl-5-(triphenylsiloxy)-7-iodo-2,6-heptadien-1-ol

(2E,6E)-(4R,5R)-7-Iodo-2,4,6-trimethyl-5-triphenylsilanyloxy-hepta-2,6-dienoic acid ethyl ester

Downstream raw materials:

(1E,3R,4R,5E,9R,10R,11R)-1-iodo-2,4,6-trimethyl-3-(triphenylsiloxy)-9-[(4-methoxybenzyloxy)methyl]-10,11-bis(4-methoxybenzyloxy)-12-(tert-butyldimethyl-siloxy)-8-oxa-1,5-dodecadiene

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