(4R,5R)-4-[(2R,3R,4R)-3,5-bis(benzyloxy)-4-methylpentan-2-yl]-2,2,5-trimethyl-1,3-dioxane

Base Information

• Chemical Name: (4R,5R)-4-[(2R,3R,4R)-3,5-bis(benzyloxy)-4-methylpentan-2-yl]-2,2,5-trimethyl-1,3-dioxane
• CAS No.: 1410935-60-2
• Molecular Formula: C₂₇H₃₈O₄
• Molecular Weight: 426.596

Synonyms:(4R,5R)-4-[(2R,3R,4R)-3,5-bis(benzyloxy)-4-methylpentan-2-yl]-2,2,5-trimethyl-1,3-dioxane

Chemical Property of (4R,5R)-4-[(2R,3R,4R)-3,5-bis(benzyloxy)-4-methylpentan-2-yl]-2,2,5-trimethyl-1,3-dioxane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of (4R,5R)-4-[(2R,3R,4R)-3,5-bis(benzyloxy)-4-methylpentan-2-yl]-2,2,5-trimethyl-1,3-dioxane

There total 7 articles about (4R,5R)-4-[(2R,3R,4R)-3,5-bis(benzyloxy)-4-methylpentan-2-yl]-2,2,5-trimethyl-1,3-dioxane 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: 93.0%

benzyl bromide (100-39-0) + (2R,3R,4R)-3-(benzyloxy)-2-methyl-4-((4R,5R)-2,2,5-trimethyl-1,3-dioxan-4-yl)pentan-1-ol → (4R,5R)-4-[(2R,3R,4R)-3,5-bis(benzyloxy)-4-methylpentan-2-yl]-2,2,5-trimethyl-1,3-dioxane (1410935-60-2)

Guidance literature:

(2R,3R,4R)-3-(benzyloxy)-2-methyl-4-((4R,5R)-2,2,5-trimethyl-1,3-dioxan-4-yl)pentan-1-ol; With sodium hydride; In tetrahydrofuran; mineral oil; for 0.166667h; Inert atmosphere; Cooling with ice;

benzyl bromide; With tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; mineral oil; for 3h; Reflux; Inert atmosphere;

DOI:10.1055/s-0032-1316561

Reference yield:

endo-3-benzyloxy-endo,endo-2,4-dimethyl-6,9-dioxabicyclo[3.2.1]non-7-one (171231-75-7) → (4R,5R)-4-[(2R,3R,4R)-3,5-bis(benzyloxy)-4-methylpentan-2-yl]-2,2,5-trimethyl-1,3-dioxane (1410935-60-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: lithium diisopropyl amide / tetrahydrofuran; hexane / -78 °C / Inert atmosphere

1.2: 3 h / Inert atmosphere

2.1: lithium aluminium tetrahydride / tetrahydrofuran / 5 h / 0 - 20 °C / Inert atmosphere

3.1: camphor-10-sulfonic acid / dichloromethane / 5 h / 20 °C / Inert atmosphere

4.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / Inert atmosphere; Cooling with ice

4.2: 3 h / Reflux; Inert atmosphere

With lithium aluminium tetrahydride; camphor-10-sulfonic acid; sodium hydride; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; mineral oil;

DOI:10.1055/s-0032-1316561

Reference yield:

endo-3-benzyloxy-endo,endo-2,4-dimethyl-exo-6-hydroxy-8-oxabicyclo[3.2.1]octane (171231-72-4) → (4R,5R)-4-[(2R,3R,4R)-3,5-bis(benzyloxy)-4-methylpentan-2-yl]-2,2,5-trimethyl-1,3-dioxane (1410935-60-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: pyridinium chlorochromate / dichloromethane / 3 h / 20 °C / Inert atmosphere

2.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 10 h / 0 - 20 °C / Inert atmosphere

3.1: lithium diisopropyl amide / tetrahydrofuran; hexane / -78 °C / Inert atmosphere

3.2: 3 h / Inert atmosphere

4.1: lithium aluminium tetrahydride / tetrahydrofuran / 5 h / 0 - 20 °C / Inert atmosphere

5.1: camphor-10-sulfonic acid / dichloromethane / 5 h / 20 °C / Inert atmosphere

6.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / Inert atmosphere; Cooling with ice

6.2: 3 h / Reflux; Inert atmosphere

With lithium aluminium tetrahydride; camphor-10-sulfonic acid; sodium hydride; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; mineral oil; 2.1: Baeyer-Villiger oxidation;

DOI:10.1055/s-0032-1316561

upstream raw materials:

benzyl bromide

2,2-dimethoxy-propane

endo-3-benzyloxy-endo,endo-2,4-dimethyl-6,9-dioxabicyclo[3.2.1]non-7-one

endo-3-benzyloxy-endo,endo-2,4-dimethyl-exo-6-hydroxy-8-oxabicyclo[3.2.1]octane

Downstream raw materials:

(2R,3R,4S,5R,6R)-5,7-bis(benzyloxy)-2,4,6-trimethylheptane-1,3-diol

(2R,3R,4S,5R,6R)-5,7-bis(benzyloxy)-3-(tert-butyldimethylsilyloxy)-2,4,6-trimethylheptyl 4-methylbenzenesulfonate

[(2R,3R,4R,5R,6R)-1,3-bis(benzyloxy)-2,4,6-trimethylnonan-5-yloxy]-tert-butyldimethylsilane

(2R,3R,4S,5R,6R)-1,3-bis(benzyloxy)-2,4,6-trimethylnonan-5-ol

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