vomifoliol acetate

Base Information

• Chemical Name: vomifoliol acetate
• CAS No.: 84551-74-6
• Molecular Formula: C₁₅H₂₂O₄
• Molecular Weight: 266.337
• Mol file: 84551-74-6.mol

Synonyms:vomifoliol acetate

Chemical Property of vomifoliol acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of vomifoliol acetate

There total 6 articles about vomifoliol acetate 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:

Acetic acid (E)-(R)-1-methyl-3-((1S,6R)-2,2,6-trimethyl-4-oxo-7-oxa-bicyclo[4.1.0]hept-1-yl)-allyl ester (437711-51-8) → vomifoliol acetate (84551-74-6)

Guidance literature:

With toluene-4-sulfonic acid; In benzene; at 20 ℃; for 17h;

DOI:10.1248/cpb.53.541

Reference yield:

Acetic acid (E)-(R)-3-((1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxa-bicyclo[4.1.0]hept-1-yl)-1-methyl-allyl ester (863032-35-3) → vomifoliol acetate (84551-74-6)

Guidance literature:

Multi-step reaction with 2 steps

1: Dess-Martin periodinane / CH₂Cl₂ / 1.5 h / 20 °C

2: 446 mg / p-TsOH*H₂O / benzene / 17 h / 20 °C

With Dess-Martin periodane; toluene-4-sulfonic acid; In dichloromethane; benzene;

DOI:10.1248/cpb.53.541

Reference yield:

(E)-(R)-4-[(R)-4-(tert-Butyl-dimethyl-silanyloxy)-2,6,6-trimethyl-cyclohex-1-enyl]-but-3-en-2-ol (863032-50-2) → vomifoliol acetate (84551-74-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 90 percent / pyridine / 3 h / 20 °C

2: 30 percent / m-chloroperoxybenzoic acid / CH₂Cl₂ / 1 h / 20 °C

3: 97 percent / HF*Py / tetrahydrofuran / 0.25 h / 0 °C

4: Dess-Martin periodinane / CH₂Cl₂ / 1.5 h / 20 °C

5: 446 mg / p-TsOH*H₂O / benzene / 17 h / 20 °C

With pyridine; Dess-Martin periodane; toluene-4-sulfonic acid; pyridine hydrogenfluoride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; benzene;

DOI:10.1248/cpb.53.541

upstream raw materials:

Acetic acid (E)-(R)-1-methyl-3-((1S,6R)-2,2,6-trimethyl-4-oxo-7-oxa-bicyclo[4.1.0]hept-1-yl)-allyl ester

Acetic acid (E)-(R)-3-((1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxa-bicyclo[4.1.0]hept-1-yl)-1-methyl-allyl ester

(E)-(R)-4-[(R)-4-(tert-Butyl-dimethyl-silanyloxy)-2,6,6-trimethyl-cyclohex-1-enyl]-but-3-en-2-ol

Acetic acid (E)-(R)-3-[(R)-4-(tert-butyl-dimethyl-silanyloxy)-2,6,6-trimethyl-cyclohex-1-enyl]-1-methyl-allyl ester

Downstream raw materials:

blumenol A

2,2-Dimethyl-propionic acid (2R,3R,4S,5R,6R)-4,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-2-[(E)-(R)-3-((S)-1-hydroxy-2,6,6-trimethyl-4-oxo-cyclohex-2-enyl)-1-methyl-allyloxy]-tetrahydro-pyran-3-yl ester

(6S,9R)-roseoside

Refernces