(2R,4S,5R,6S)-7-(4-methoxybenzyloxy)-5-(tert-butyldimethylsilyloxy)-2,4,6-trimethylheptanal

Base Information

• Chemical Name: (2R,4S,5R,6S)-7-(4-methoxybenzyloxy)-5-(tert-butyldimethylsilyloxy)-2,4,6-trimethylheptanal
• CAS No.: 792911-19-4
• Molecular Formula: C₂₄H₄₂O₄Si
• Molecular Weight: 422.681
• Mol file: 792911-19-4.mol

Synonyms:(2R,4S,5R,6S)-7-(4-methoxybenzyloxy)-5-(tert-butyldimethylsilyloxy)-2,4,6-trimethylheptanal

Chemical Property of (2R,4S,5R,6S)-7-(4-methoxybenzyloxy)-5-(tert-butyldimethylsilyloxy)-2,4,6-trimethylheptanal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,4S,5R,6S)-7-(4-methoxybenzyloxy)-5-(tert-butyldimethylsilyloxy)-2,4,6-trimethylheptanal

There total 6 articles about (2R,4S,5R,6S)-7-(4-methoxybenzyloxy)-5-(tert-butyldimethylsilyloxy)-2,4,6-trimethylheptanal 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: 80.0%

(2R,4S,5R,6S)-7-(4-methoxybenzyloxy)-5-(tert-butyldimethylsilyloxy)-2,4,6-trimethylheptan-1-ol (792921-75-6) → (2R,4S,5R,6S)-7-(4-methoxybenzyloxy)-5-(tert-butyldimethylsilyloxy)-2,4,6-trimethylheptanal (792911-19-4)

Guidance literature:

With tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide; In dichloromethane; Molecular sieve;

DOI:10.1002/ejoc.200801234

Reference yield:

(-)-(2S,3R,4S)-3-((tert-butyldimethylsilyl)oxy)-5-((4-methoxybenzyl)oxy)-2,4-dimethylpentan-1-ol (792911-22-9) → (2R,4S,5R,6S)-7-(4-methoxybenzyloxy)-5-(tert-butyldimethylsilyloxy)-2,4,6-trimethylheptanal (792911-19-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 86 percent / PPh₃; I₂; imidazole / toluene / 0.25 h / 0 °C

2.1: LiCl; lithium diisopropylamide / tetrahydrofuran / -78 - 20 °C

2.2: tetrahydrofuran / 18 h / 0 - 20 °C

3.1: LiNH₂BH₃ / tetrahydrofuran / 18 h / 0 - 20 °C

4.1: Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 2 h / 0 °C

With 1H-imidazole; lithium amidotrihydroborate; iodine; sodium hydrogencarbonate; Dess-Martin periodane; triphenylphosphine; lithium chloride; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; toluene; 1.1: modified Mitsunobu reaction;

DOI:10.1002/anie.200460589

Reference yield:

(2S,3S,4S)-1,3-bis[(tert-butyldimethylsilyl)oxy]-5-[(4-Methoxybenzyl)oxy]-2,4-dimethylpentane (792911-21-8) → (2R,4S,5R,6S)-7-(4-methoxybenzyloxy)-5-(tert-butyldimethylsilyloxy)-2,4,6-trimethylheptanal (792911-19-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 93 percent / p-toluenesulfonic acid / tetrahydrofuran; H₂O / 24 h

2.1: 86 percent / PPh₃; I₂; imidazole / toluene / 0.25 h / 0 °C

3.1: LiCl; lithium diisopropylamide / tetrahydrofuran / -78 - 20 °C

3.2: tetrahydrofuran / 18 h / 0 - 20 °C

4.1: LiNH₂BH₃ / tetrahydrofuran / 18 h / 0 - 20 °C

5.1: Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 2 h / 0 °C

With 1H-imidazole; lithium amidotrihydroborate; iodine; sodium hydrogencarbonate; Dess-Martin periodane; toluene-4-sulfonic acid; triphenylphosphine; lithium chloride; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; water; toluene; 2.1: modified Mitsunobu reaction;

DOI:10.1002/anie.200460589

upstream raw materials:

(2R,4S,5R,6S)-7-(4-methoxybenzyloxy)-5-(tert-butyldimethylsilyloxy)-2,4,6-trimethylheptan-1-ol

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

(2S,3S,4S)-1,3-bis[(tert-butyldimethylsilyl)oxy]-5-[(4-Methoxybenzyl)oxy]-2,4-dimethylpentane

(2R,4S,5R,6S)-7-(4-methoxybenzyloxy)-5-(tert-butyldimethylsilyloxy)-N-((1S,2S)-1-hydroxy-1-phenylpropan-2-yl)-N,2,4,6-tetramethylheptanamide

Downstream raw materials:

(2S,3S,4R,8R,10S,11R,12S,E)-13-(4-methoxybenzyloxy)-11-(tert-butyldimethylsilyloxy)-1-(tert-butyldiphenylsilyloxy)-2,4,8,10,12-pentamethyl-3-(trimethylsilyloxy)tridec-6-en-5-one

(3Z,9E)-(5S,6S,7R,11R,13S,14R,15S)-14-(tert-Butyl-dimethyl-silanyloxy)-6,16-bis-(4-methoxy-benzyloxy)-5,7,11,13,15-pentamethyl-hexadeca-1,3,9-trien-8-one