7',8'-Dihydroobolactone

Base Information

• Chemical Name: 7',8'-Dihydroobolactone
• CAS No.: 1240403-82-0
• Molecular Formula: C₁₉H₂₀O₄
• Molecular Weight: 312.365
• Mol file: 1240403-82-0.mol

Synonyms:

Chemical Property of 7',8'-Dihydroobolactone

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

7',8'-Dihydroobolactone 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 7',8'-Dihydroobolactone

There total 8 articles about 7',8'-Dihydroobolactone 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:

(7S,E)-9-(tert-butyldimethylsilyloxy)-1-phenylnon-1-en-4-yne-3,7-diol → (R)-6-[((R)-4-oxo-6-phenethyl-3,4-dihydro-2H-pyran-2-yl)methyl]-5,6-dihydro-2H-pyran-2-one (1240403-82-0) + (S)-6-[((R)-4-oxo-6-phenethyl-3,4-dihydro-2H-pyran-2-yl)methyl]-5,6-dihydro-2H-pyran-2-one

Guidance literature:

Multi-step reaction with 6 steps

1: manganese(IV) oxide / dichloromethane / 6 h / 20 °C

2: toluene-4-sulfonic acid / methanol / 1 h / 20 °C

3: Dess-Martin periodane / dichloromethane / 3 h / 0 °C

4: 1,2-Diiodoethane; zinc / tetrahydrofuran / 1 h / 20 °C

5: triethylamine; dmap / dichloromethane / 2 h / 0 °C / Inert atmosphere

6: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 6 h / Inert atmosphere; Reflux

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; manganese(IV) oxide; 1,2-Diiodoethane; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; zinc; In tetrahydrofuran; methanol; dichloromethane; toluene; 4: |Barbier Coupling Reaction;

DOI:10.1039/d1nj03990c

Reference yield:

(R)-9-(tert-butyldimethylsilyloxy)-7-hydroxy-1-phenylnon-4-yn-3-one → (R)-6-[((R)-4-oxo-6-phenethyl-3,4-dihydro-2H-pyran-2-yl)methyl]-5,6-dihydro-2H-pyran-2-one (1240403-82-0) + (S)-6-[((R)-4-oxo-6-phenethyl-3,4-dihydro-2H-pyran-2-yl)methyl]-5,6-dihydro-2H-pyran-2-one

Guidance literature:

Multi-step reaction with 5 steps

1: toluene-4-sulfonic acid / methanol / 1 h / 20 °C

2: Dess-Martin periodane / dichloromethane / 3 h / 0 °C

3: 1,2-Diiodoethane; zinc / tetrahydrofuran / 1 h / 20 °C

4: triethylamine; dmap / dichloromethane / 2 h / 0 °C / Inert atmosphere

5: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 6 h / Inert atmosphere; Reflux

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; 1,2-Diiodoethane; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; zinc; In tetrahydrofuran; methanol; dichloromethane; toluene; 3: |Barbier Coupling Reaction;

DOI:10.1039/d1nj03990c

Reference yield:

(R)-2-(2-hydroxyethyl)-6-phenethyl-2,3-dihydro-4H-pyran-4-one → (R)-6-[((R)-4-oxo-6-phenethyl-3,4-dihydro-2H-pyran-2-yl)methyl]-5,6-dihydro-2H-pyran-2-one (1240403-82-0) + (S)-6-[((R)-4-oxo-6-phenethyl-3,4-dihydro-2H-pyran-2-yl)methyl]-5,6-dihydro-2H-pyran-2-one

Guidance literature:

Multi-step reaction with 4 steps

1: Dess-Martin periodane / dichloromethane / 3 h / 0 °C

2: 1,2-Diiodoethane; zinc / tetrahydrofuran / 1 h / 20 °C

3: triethylamine; dmap / dichloromethane / 2 h / 0 °C / Inert atmosphere

4: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 6 h / Inert atmosphere; Reflux

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; 1,2-Diiodoethane; Dess-Martin periodane; triethylamine; zinc; In tetrahydrofuran; dichloromethane; toluene; 2: |Barbier Coupling Reaction;

DOI:10.1039/d1nj03990c

upstream raw materials:

((S)-3-hydroxyhex-5-ynyloxy)(tert-butyl)dimethylsilane

C₁₅H₃₂O₂Si₂

Refernces