(2R,4R)-2-(benzyloxy)-5-((tert-butyldimethylsilyl)oxy)-4-methylpentan-1-ol

Base Information

• Chemical Name: (2R,4R)-2-(benzyloxy)-5-((tert-butyldimethylsilyl)oxy)-4-methylpentan-1-ol
• CAS No.: 1431879-89-8
• Molecular Formula: C₁₉H₃₄O₃Si
• Molecular Weight: 338.563

Synonyms:(2R,4R)-2-(benzyloxy)-5-((tert-butyldimethylsilyl)oxy)-4-methylpentan-1-ol

Chemical Property of (2R,4R)-2-(benzyloxy)-5-((tert-butyldimethylsilyl)oxy)-4-methylpentan-1-ol

Chemical Property:

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Technology Process of (2R,4R)-2-(benzyloxy)-5-((tert-butyldimethylsilyl)oxy)-4-methylpentan-1-ol

There total 3 articles about (2R,4R)-2-(benzyloxy)-5-((tert-butyldimethylsilyl)oxy)-4-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: 70.0%

C19H32O3Si (1431879-90-1) → (2R,4R)-2-(benzyloxy)-5-((tert-butyldimethylsilyl)oxy)-4-methylpentan-1-ol (1431879-89-8)

Guidance literature:

With diisobutylaluminium hydride; In dichloromethane; toluene; at 0 - 20 ℃; for 1h; Inert atmosphere;

DOI:10.1021/ol400487e

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → (2R,4R)-2-(benzyloxy)-5-((tert-butyldimethylsilyl)oxy)-4-methylpentan-1-ol (1431879-89-8)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridinium p-toluenesulfonate / dichloromethane / 2 h / 20 °C / Inert atmosphere

2: diisobutylaluminium hydride / dichloromethane; toluene / 1 h / 0 - 20 °C / Inert atmosphere

With pyridinium p-toluenesulfonate; diisobutylaluminium hydride; In dichloromethane; toluene;

DOI:10.1021/ol400487e

Reference yield:

(2R,4R)-5-((tert-butyldimethylsilyl)oxy)-4-methylpentane-1,2-diol (1006724-46-4) → (2R,4R)-2-(benzyloxy)-5-((tert-butyldimethylsilyl)oxy)-4-methylpentan-1-ol (1431879-89-8)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridinium p-toluenesulfonate / dichloromethane / 2 h / 20 °C / Inert atmosphere

2: diisobutylaluminium hydride / dichloromethane; toluene / 1 h / 0 - 20 °C / Inert atmosphere

With pyridinium p-toluenesulfonate; diisobutylaluminium hydride; In dichloromethane; toluene;

DOI:10.1021/ol400487e

upstream raw materials:

(2R,4R)-5-((tert-butyldimethylsilyl)oxy)-4-methylpentane-1,2-diol

benzaldehyde dimethyl acetal

C₁₉H₃₂O₃Si

Downstream raw materials:

(2R,4R)-2-(benzyloxy)-5-((tert-butyldimethylsilyl)oxy)-4-methylpentanal

(2S,5R,6R,8R)-6-(benzyloxy)-9-((tert-butyldimethylsilyl)oxy)-5-hydroxy-8-methyl-3-oxo-2-((triisopropylsilyl)oxy)nonyl pivalate

(2S,5R,6R,8R)-5-acetoxy-6-(benzyloxy)-9-((tert-butyldimethylsilyl)oxy)-8-methyl-3-oxo-2-((triisopropylsilyl)oxy)nonyl pivalate

(S)-2-((2S,4R,5R)-4-acetoxy-5-((R)-5-((2R,6R)-6-((E)-5-((tertbutyldiphenylsilyl)oxy)pent-1-en-1-yl)-2-methoxy-3,6-dihydro-2H-pyran-2-yl)-2-methyl-3-oxopent-4-yn-1-yl)tetrahydrofuran-2-yl)-2-((triisopropylsilyl)oxy)ethylpivalate

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