endo-3-benzyloxy-endo,endo-2,4-dimethyl-8-oxabicyclo-[3.2.1]-octan-6-one

Base Information

• Chemical Name: endo-3-benzyloxy-endo,endo-2,4-dimethyl-8-oxabicyclo-[3.2.1]-octan-6-one
• CAS No.: 760978-01-6
• Molecular Formula: C₁₆H₂₀O₃
• Molecular Weight: 260.333
• Mol file: 760978-01-6.mol

Synonyms:endo-3-benzyloxy-endo,endo-2,4-dimethyl-8-oxabicyclo-[3.2.1]-octan-6-one

Chemical Property of endo-3-benzyloxy-endo,endo-2,4-dimethyl-8-oxabicyclo-[3.2.1]-octan-6-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of endo-3-benzyloxy-endo,endo-2,4-dimethyl-8-oxabicyclo-[3.2.1]-octan-6-one

There total 2 articles about endo-3-benzyloxy-endo,endo-2,4-dimethyl-8-oxabicyclo-[3.2.1]-octan-6-one 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: 94.0%

endo-3-benzyloxy-endo,endo-2,4-dimethyl-exo-6-hydroxy-8-oxabicyclo[3.2.1]octane (171231-72-4) → endo-3-benzyloxy-endo,endo-2,4-dimethyl-8-oxabicyclo-[3.2.1]-octan-6-one (760978-01-6)

Guidance literature:

With pyridinium chlorochromate; In dichloromethane; at 20 ℃;

DOI:10.1016/j.tetlet.2004.06.121

Reference yield:

(1R,2R,3r,4S,5S)-3-(benzyloxy)-2,4-dimethyl-8-oxa-bicyclo[3.2.1]oct-6-ene (96691-92-8) → endo-3-benzyloxy-endo,endo-2,4-dimethyl-8-oxabicyclo-[3.2.1]-octan-6-one (760978-01-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: (-)-diisopinocamphenylborane / tetrahydrofuran / 24 h / -23 °C

1.2: aq. NaOH; H₂O₂ / 6 h / 20 °C

2.1: pyridinium chlorochromate / CH₂Cl₂ / 3 h / 20 °C

With diisopinocampheylborane; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane;

DOI:10.1055/s-2007-982556

Reference yield: 97.0%

endo-3-benzyloxy-endo,endo-2,4-dimethyl-8-oxabicyclo-[3.2.1]-octan-6-one (760978-01-6) → endo-3-benzyloxy-endo,endo-2,4-dimethyl-6,9-dioxabicyclo[3.2.1]non-7-one (171231-75-7)

Guidance literature:

With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20 ℃; for 10h; Inert atmosphere;

DOI:10.1055/s-0032-1316561

upstream raw materials:

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

(1R,2R,3r,4S,5S)-3-(benzyloxy)-2,4-dimethyl-8-oxa-bicyclo[3.2.1]oct-6-ene

Downstream raw materials:

(1S,5R,6S,7S,8S)-7-Benzyloxy-6,8-dimethyl-2,9-dioxa-bicyclo[3.3.1]nonan-3-one

(+)-prelactone B

(3R,4S,5R,6R)-5-(benzyloxy)-4,6-dimethylheptane-1,3,7-triol

(2R,3R,4S)-3-(benzyloxy)-4-((R)-2,2-dimethyl-1,3-dioxan-4-yl)-2-methylpentan-1-ol