2-benzyloxy-5-(tetrahydropyran-2-yloxy)-4-(tetrahydropyran-2-yloxymethyl)pentanale

Base Information

• Chemical Name: 2-benzyloxy-5-(tetrahydropyran-2-yloxy)-4-(tetrahydropyran-2-yloxymethyl)pentanale
• CAS No.: 204325-71-3
• Molecular Formula: C₂₃H₃₄O₆
• Molecular Weight: 406.519
• Mol file: 204325-71-3.mol

Synonyms:

Chemical Property of 2-benzyloxy-5-(tetrahydropyran-2-yloxy)-4-(tetrahydropyran-2-yloxymethyl)pentanale

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-benzyloxy-5-(tetrahydropyran-2-yloxy)-4-(tetrahydropyran-2-yloxymethyl)pentanale

There total 3 articles about 2-benzyloxy-5-(tetrahydropyran-2-yloxy)-4-(tetrahydropyran-2-yloxymethyl)pentanale 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:

1,3-bis[(tetrahydro-2H-pyran-2-yl)oxy]-2-propanone (32888-40-7) → 2-benzyloxy-5-(tetrahydropyran-2-yloxy)-4-(tetrahydropyran-2-yloxymethyl)pentanale (204325-71-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 83 percent / diethyl ether / 2.5 h / 0 °C

2: 1.) NaH, tetra-n-butylammonium iodide / 1.) DMF, RT, 10 min, 2.) DMF, RT, 5 h

3: 1.) OsO₄, 2.) NaIO₄ / 1.) ether, water, RT, 5 min, 2.) ether, water, RT, 3 h

With sodium periodate; osmium(VIII) oxide; tetra-(n-butyl)ammonium iodide; sodium hydride; In diethyl ether;

DOI:10.1248/cpb.46.217

Reference yield:

2-benzyloxy-1-(tetrahydropyran-2-yloxy)-2-(tetrahydropyran-2-yloxymethyl)-5-hexene (204325-70-2) → 2-benzyloxy-5-(tetrahydropyran-2-yloxy)-4-(tetrahydropyran-2-yloxymethyl)pentanale (204325-71-3)

Guidance literature:

With sodium periodate; osmium(VIII) oxide; Yield given. Multistep reaction; 1.) ether, water, RT, 5 min, 2.) ether, water, RT, 3 h;

DOI:10.1248/cpb.46.217

Reference yield:

1-(tetrahydropyran-2-yloxy)-2-(tetrahydropyran-2-yloxymethyl)-5-hexen-2-ol (204325-69-9) → 2-benzyloxy-5-(tetrahydropyran-2-yloxy)-4-(tetrahydropyran-2-yloxymethyl)pentanale (204325-71-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) NaH, tetra-n-butylammonium iodide / 1.) DMF, RT, 10 min, 2.) DMF, RT, 5 h

2: 1.) OsO₄, 2.) NaIO₄ / 1.) ether, water, RT, 5 min, 2.) ether, water, RT, 3 h

With sodium periodate; osmium(VIII) oxide; tetra-(n-butyl)ammonium iodide; sodium hydride;

DOI:10.1248/cpb.46.217

upstream raw materials:

2-benzyloxy-1-(tetrahydropyran-2-yloxy)-2-(tetrahydropyran-2-yloxymethyl)-5-hexene

1,3-bis[(tetrahydro-2H-pyran-2-yl)oxy]-2-propanone

1-(tetrahydropyran-2-yloxy)-2-(tetrahydropyran-2-yloxymethyl)-5-hexen-2-ol

Downstream raw materials:

(R_S)-5-benzyloxy-6-(tetrahydropyran-2-yloxy)-5-(tetrahydropyran-2-yloxymethyl)-1-(p-toluenesulfinyl)hexan-2-ol

(1S,5R)-5-methyl-1-para-toluenesulfonyloxymethyl-6,8-dioxabicyclo[3.2.1]octane

Toluene-4-sulfonic acid (S)-2-benzyloxy-2-hydroxymethyl-6-oxo-heptyl ester

(R_S)-5-benzyloxy-5-hydroxymethyl-2-methoxy-2-(p-toluenesulfinyl-methyl)tetrahydropyran