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

Base Information

• Chemical Name: tert-butyl{[(4R,5S,6R,7R,1E)-2-iodo-7-methoxy-9-[(4-methoxybenzyl)oxy]-4,6-dimethylnon-2-en-5-yl]oxy}dimethylsilane
• CAS No.: 1427556-42-0
• Molecular Formula: C₂₆H₄₅IO₄Si
• Molecular Weight: 576.631
• Mol file: 1427556-42-0.mol

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

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

There total 12 articles about tert-butyl{[(4R,5S,6R,7R,1E)-2-iodo-7-methoxy-9-[(4-methoxybenzyl)oxy]-4,6-dimethylnon-2-en-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: 88.0%

tert-butyl{[(4R,5S,6R,7R)-7-methoxy-9-[(4-methoxybenzyl)oxy]-4,6-dimethylnon-2-yn-5-yl]oxy}dimethylsilane (1427556-40-8) → tert-butyl{[(4R,5S,6R,7R,1E)-2-iodo-7-methoxy-9-[(4-methoxybenzyl)oxy]-4,6-dimethylnon-2-en-5-yl]oxy}dimethylsilane (1427556-42-0)

Guidance literature:

tert-butyl{[(4R,5S,6R,7R)-7-methoxy-9-[(4-methoxybenzyl)oxy]-4,6-dimethylnon-2-yn-5-yl]oxy}dimethylsilane; With zirconocene dichloride; diisobutylaluminium hydride; In tetrahydrofuran; toluene; at 0 - 20 ℃; Inert atmosphere;

With iodine; In tetrahydrofuran; toluene; at -78 ℃; for 0.5h; Inert atmosphere;

DOI:10.1055/s-0032-1317700

Reference yield:

((2R,3R)-3-(2-(4-methoxybenzyloxy)ethyl)oxiran-2-yl)methanol (242808-65-7) → tert-butyl{[(4R,5S,6R,7R,1E)-2-iodo-7-methoxy-9-[(4-methoxybenzyl)oxy]-4,6-dimethylnon-2-en-5-yl]oxy}dimethylsilane (1427556-42-0)

Guidance literature:

Multi-step reaction with 12 steps

1.1: copper(l) iodide / diethyl ether / 0.25 h / 0 °C / Inert atmosphere

1.2: 3 h / -40 - 0 °C / Inert atmosphere

1.3: 1 h / Inert atmosphere

2.1: 1H-imidazole / dichloromethane / 0.25 h / 0 °C / Inert atmosphere

2.2: 1 h / 0 °C / Inert atmosphere

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

3.2: 2 h / 20 °C / Inert atmosphere

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

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

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

6.2: 1 h / 0 °C / Inert atmosphere

6.3: 1.5 h / -78 - 0 °C / Inert atmosphere

7.1: 2,6-dimethylpyridine / dichloromethane / 0.33 h / 0 °C / Inert atmosphere

7.2: Inert atmosphere

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

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

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

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

11.2: 1 h / -78 °C / Inert atmosphere

12.1: zirconocene dichloride; diisobutylaluminium hydride / tetrahydrofuran; toluene / 0 - 20 °C / Inert atmosphere

12.2: 0.5 h / -78 °C / Inert atmosphere

With 1H-imidazole; 2,6-dimethylpyridine; methanol; copper(l) iodide; lithium borohydride; n-butyllithium; zirconocene dichloride; oxalyl dichloride; carbon tetrabromide; di-n-butylboryl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine; triphenylphosphine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; dimethyl sulfoxide; toluene; 6.3: |Evans Aldol Reaction;

DOI:10.1055/s-0032-1317700

Reference yield:

(S)-4-benzyl-3-[(2S,3R,4R,5R)-3-[(tert-butyldimethylsilyl)oxy]-5-methoxy-7-[(4-methoxybenzyl)oxy]-2,4-dimethylheptanoyl]oxazolidin-2-one → tert-butyl{[(4R,5S,6R,7R,1E)-2-iodo-7-methoxy-9-[(4-methoxybenzyl)oxy]-4,6-dimethylnon-2-en-5-yl]oxy}dimethylsilane (1427556-42-0)

Guidance literature:

Multi-step reaction with 5 steps

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

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

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

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

4.2: 1 h / -78 °C / Inert atmosphere

5.1: zirconocene dichloride; diisobutylaluminium hydride / tetrahydrofuran; toluene / 0 - 20 °C / Inert atmosphere

5.2: 0.5 h / -78 °C / Inert atmosphere

With methanol; lithium borohydride; n-butyllithium; zirconocene dichloride; carbon tetrabromide; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine; triphenylphosphine; In tetrahydrofuran; hexane; dichloromethane; toluene;

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

(2S,3R)-1-[(tert-butyldimethylsilyl)oxy]-5-[(4-methoxybenzyl)oxy]-2-methylpentan-3-ol

(2R,3R)-3-methoxy-5-(4'-methoxybenzyloxy)-2-methylpentanal

Downstream raw materials:

(4R,5R)-methyl 5-{(1E,3R,7S,9E,11R,12S,13R,14R)-12-[(tert-butyldimethylsilyl)oxy]-8-hydroxy-14-methoxy-16-[(4-methoxybenzyl)oxy]-3,7,9,11,13-pentamethylhexadeca-1,9-dienyl}-2,2-dimethyl-1,3-dioxalone-4-carboxylate

(4R,5R)-methyl 5-{(1E,3R,7S,9E,11R,12S,13R,14R)-12-[(tert-butyldimethylsilyl)oxy]-8-hydroxy-14-methoxy-16-[(4-methoxybenzyl)oxy]-3,7,9,11,13-pentamethylhexadeca-1,9-dienyl}-2,2-dimethyl-1,3-dioxalone-4-carboxylate