tert-butyl{[(4R,5S,6R,7R)-7-methoxy-9-[(4-methoxybenzyl)oxy]-4,6-dimethylnon-2-yn-5-yl]oxy}dimethylsilane

Base Information

• Chemical Name: tert-butyl{[(4R,5S,6R,7R)-7-methoxy-9-[(4-methoxybenzyl)oxy]-4,6-dimethylnon-2-yn-5-yl]oxy}dimethylsilane
• CAS No.: 1427556-40-8
• Molecular Formula: C₂₆H₄₄O₄Si
• Molecular Weight: 448.718
• Mol file: 1427556-40-8.mol

Synonyms:tert-butyl{[(4R,5S,6R,7R)-7-methoxy-9-[(4-methoxybenzyl)oxy]-4,6-dimethylnon-2-yn-5-yl]oxy}dimethylsilane

Chemical Property of tert-butyl{[(4R,5S,6R,7R)-7-methoxy-9-[(4-methoxybenzyl)oxy]-4,6-dimethylnon-2-yn-5-yl]oxy}dimethylsilane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl{[(4R,5S,6R,7R)-7-methoxy-9-[(4-methoxybenzyl)oxy]-4,6-dimethylnon-2-yn-5-yl]oxy}dimethylsilane

There total 11 articles about tert-butyl{[(4R,5S,6R,7R)-7-methoxy-9-[(4-methoxybenzyl)oxy]-4,6-dimethylnon-2-yn-5-yl]oxy}dimethylsilane 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: 94.0%

tert-butyl{[(3R,4S,5R,6R)-1,1-dibromo-6-methoxy-8-[(4-methoxybenzyl)oxy]-3,5-dimethyloct-1-en-4-yl]oxy}dimethylsilane (1427556-38-4) + methyl iodide (74-88-4) → tert-butyl{[(4R,5S,6R,7R)-7-methoxy-9-[(4-methoxybenzyl)oxy]-4,6-dimethylnon-2-yn-5-yl]oxy}dimethylsilane (1427556-40-8)

Guidance literature:

tert-butyl{[(3R,4S,5R,6R)-1,1-dibromo-6-methoxy-8-[(4-methoxybenzyl)oxy]-3,5-dimethyloct-1-en-4-yl]oxy}dimethylsilane; With n-butyllithium; In tetrahydrofuran; hexane; at -78 - -25 ℃; for 1h; Inert atmosphere;

methyl iodide; at -78 ℃; for 1h; Inert atmosphere;

DOI:10.1055/s-0032-1317700

Reference yield:

(2S,3R)-5-[(4-methoxybenzyl)oxy]-2-methylpentane-1,3-diol (1427556-29-3) → tert-butyl{[(4R,5S,6R,7R)-7-methoxy-9-[(4-methoxybenzyl)oxy]-4,6-dimethylnon-2-yn-5-yl]oxy}dimethylsilane (1427556-40-8)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 1H-imidazole / dichloromethane / 0.25 h / 0 °C / Inert atmosphere

1.2: 1 h / 0 °C / Inert atmosphere

2.1: sodium hydride / tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere

2.2: 2 h / 20 °C / Inert atmosphere

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 °C / Inert atmosphere

4.1: oxalyl dichloride; triethylamine / dichloromethane; dimethyl sulfoxide / 2.5 h / -78 - 20 °C / Inert atmosphere

5.1: di-n-butylboryl trifluoromethanesulfonate / dichloromethane / 0.17 h / 0 °C / Inert atmosphere

5.2: 1 h / 0 °C / Inert atmosphere

5.3: 1.5 h / -78 - 0 °C / Inert atmosphere

6.1: 2,6-dimethylpyridine / dichloromethane / 0.33 h / 0 °C / Inert atmosphere

6.2: Inert atmosphere

7.1: lithium borohydride; methanol / tetrahydrofuran / 0.75 h / 0 °C / Inert atmosphere

8.1: Dess-Martin periodane; sodium hydrogencarbonate / dichloromethane / 1 h / 0 °C / Inert atmosphere

9.1: triethylamine; carbon tetrabromide; triphenylphosphine / dichloromethane / -10 °C / Inert atmosphere

10.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 - -25 °C / Inert atmosphere

10.2: 1 h / -78 °C / Inert atmosphere

With 1H-imidazole; 2,6-dimethylpyridine; methanol; lithium borohydride; n-butyllithium; oxalyl dichloride; carbon tetrabromide; di-n-butylboryl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; sodium hydride; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine; triphenylphosphine; In tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide; 5.3: |Evans Aldol Reaction;

DOI:10.1055/s-0032-1317700

Reference yield:

(2R,3R)-3-methoxy-5-(4'-methoxybenzyloxy)-2-methylpentanal (603994-09-8) → tert-butyl{[(4R,5S,6R,7R)-7-methoxy-9-[(4-methoxybenzyl)oxy]-4,6-dimethylnon-2-yn-5-yl]oxy}dimethylsilane (1427556-40-8)

Guidance literature:

Multi-step reaction with 6 steps

1.1: di-n-butylboryl trifluoromethanesulfonate / dichloromethane / 0.17 h / 0 °C / Inert atmosphere

1.2: 1 h / 0 °C / Inert atmosphere

1.3: 1.5 h / -78 - 0 °C / Inert atmosphere

2.1: 2,6-dimethylpyridine / dichloromethane / 0.33 h / 0 °C / Inert atmosphere

2.2: Inert atmosphere

3.1: lithium borohydride; methanol / tetrahydrofuran / 0.75 h / 0 °C / Inert atmosphere

4.1: Dess-Martin periodane; sodium hydrogencarbonate / dichloromethane / 1 h / 0 °C / Inert atmosphere

5.1: triethylamine; carbon tetrabromide; triphenylphosphine / dichloromethane / -10 °C / Inert atmosphere

6.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 - -25 °C / Inert atmosphere

6.2: 1 h / -78 °C / Inert atmosphere

With 2,6-dimethylpyridine; methanol; lithium borohydride; n-butyllithium; carbon tetrabromide; di-n-butylboryl trifluoromethanesulfonate; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine; triphenylphosphine; In tetrahydrofuran; hexane; dichloromethane; 1.3: |Evans Aldol Reaction;

DOI:10.1055/s-0032-1317700

upstream raw materials:

(2S,3R)-5-[(4-methoxybenzyl)oxy]-2-methylpentane-1,3-diol

((2R,3R)-3-(2-(4-methoxybenzyloxy)ethyl)oxiran-2-yl)methanol

tert-butyl{[(3R,4S,5R,6R)-1,1-dibromo-6-methoxy-8-[(4-methoxybenzyl)oxy]-3,5-dimethyloct-1-en-4-yl]oxy}dimethylsilane

methyl iodide

Downstream raw materials:

tert-butyl{[(4R,5S,6R,7R,1E)-2-iodo-7-methoxy-9-[(4-methoxybenzyl)oxy]-4,6-dimethylnon-2-en-5-yl]oxy}dimethylsilane