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

Base Information

• Chemical Name: (2S,3R)-3-methoxy-5-[(4-methoxybenzyl)oxy]-2-methylpentan-1-ol
• CAS No.: 1427556-32-8
• Molecular Formula: C₁₅H₂₄O₄
• Molecular Weight: 268.353
• Mol file: 1427556-32-8.mol

Synonyms:(2S,3R)-3-methoxy-5-[(4-methoxybenzyl)oxy]-2-methylpentan-1-ol

Chemical Property of (2S,3R)-3-methoxy-5-[(4-methoxybenzyl)oxy]-2-methylpentan-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-3-methoxy-5-[(4-methoxybenzyl)oxy]-2-methylpentan-1-ol

There total 12 articles about (2S,3R)-3-methoxy-5-[(4-methoxybenzyl)oxy]-2-methylpentan-1-ol 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: 85.0%

tert-butyl{[(2S,3R)-3-methoxy-5-[(4-methoxybenzyl)oxy]-2-methylpentyl]oxy}dimethylsilane (1427556-31-7) → (2S,3R)-3-methoxy-5-[(4-methoxybenzyl)oxy]-2-methylpentan-1-ol (1427556-32-8)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; Inert atmosphere;

DOI:10.1055/s-0032-1317700

Reference yield: 78.0%

tert-butyl((2S,3R)-3-methoxy-5-(4-methoxybenzyloxy)-2-methylpentyloxy)diphenylsilane → (2S,3R)-3-methoxy-5-[(4-methoxybenzyl)oxy]-2-methylpentan-1-ol (1427556-32-8)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 20 ℃; for 3h;

DOI:10.1016/j.tetlet.2015.03.002

Reference yield:

(2S,3R)-5-[(4-methoxybenzyl)oxy]-2-methylpentane-1,3-diol (1427556-29-3) → (2S,3R)-3-methoxy-5-[(4-methoxybenzyl)oxy]-2-methylpentan-1-ol (1427556-32-8)

Guidance literature:

Multi-step reaction with 3 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

With 1H-imidazole; tetrabutyl ammonium fluoride; sodium hydride; In tetrahydrofuran; dichloromethane;

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

tert-butyl{[(2S,3R)-3-methoxy-5-[(4-methoxybenzyl)oxy]-2-methylpentyl]oxy}dimethylsilane

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

(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

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