(Z)-7-((3aR,5R,6R,6aR)-6-Benzyloxy-2,2,6-trimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-4-methyl-hept-4-enenitrile

Base Information

• Chemical Name: (Z)-7-((3aR,5R,6R,6aR)-6-Benzyloxy-2,2,6-trimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-4-methyl-hept-4-enenitrile
• CAS No.: 116726-65-9
• Molecular Formula: C₂₃H₃₁NO₄
• Molecular Weight: 385.503

Synonyms:(Z)-7-((3aR,5R,6R,6aR)-6-Benzyloxy-2,2,6-trimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-4-methyl-hept-4-enenitrile

Chemical Property of (Z)-7-((3aR,5R,6R,6aR)-6-Benzyloxy-2,2,6-trimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-4-methyl-hept-4-enenitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-7-((3aR,5R,6R,6aR)-6-Benzyloxy-2,2,6-trimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-4-methyl-hept-4-enenitrile

There total 12 articles about (Z)-7-((3aR,5R,6R,6aR)-6-Benzyloxy-2,2,6-trimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-4-methyl-hept-4-enenitrile 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:

1,2;5,6-di-O-isopropylidene-3-C-methyl-α-D-allofuranose (35784-67-9) → (Z)-7-((3aR,5R,6R,6aR)-6-Benzyloxy-2,2,6-trimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-4-methyl-hept-4-enenitrile (116726-65-9)

Guidance literature:

Multi-step reaction with 12 steps

1: 1.) KH / 1.) THF, RT, 1 h, 2.) reflux, 8 h

2: 90 percent / 90percent AcOH / 4 h / 60 °C

3: 100 percent / Celite, Pb(AcO)4 / benzene / 0.5 h / Ambient temperature

4: 88 percent / tetrahydrofuran / 3 h

5: 96 percent / H₂ / 5percent Pd/C / methanol / 3 h

6: 79 percent / DIBAL / toluene / 1 h / -78 °C

7: 1.) tert-BuLi / 1.) pentane, ether, -65 deg C, 30 min, 2.) 30 min

9: 100 percent / triethylamine / CH₂Cl₂ / 0.67 h / Ambient temperature

10: 90 percent / dimethylsulfoxide / 3 h / 70 °C

11: 93 percent / tetrabutylammonium fluoride / tetrahydrofuran / 18 h

12: 1.) KH / 1.) THF, 1 h, 2.) 5 h

With lead(IV) acetate; Celite; tetrabutyl ammonium fluoride; hydrogen; tert.-butyl lithium; potassium hydride; diisobutylaluminium hydride; acetic acid; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; toluene; benzene;

DOI:10.1021/jo00260a016

Reference yield:

(R)-1-[(3aR,5R,6R,6aR)-6-(tert-Butyl-diphenyl-silanyloxy)-2,2,6-trimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-ethane-1,2-diol (116726-54-6) → (Z)-7-((3aR,5R,6R,6aR)-6-Benzyloxy-2,2,6-trimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-4-methyl-hept-4-enenitrile (116726-65-9)

Guidance literature:

Multi-step reaction with 10 steps

1: 100 percent / Celite, Pb(AcO)4 / benzene / 0.5 h / Ambient temperature

2: 88 percent / tetrahydrofuran / 3 h

3: 96 percent / H₂ / 5percent Pd/C / methanol / 3 h

4: 79 percent / DIBAL / toluene / 1 h / -78 °C

5: 1.) tert-BuLi / 1.) pentane, ether, -65 deg C, 30 min, 2.) 30 min

7: 100 percent / triethylamine / CH₂Cl₂ / 0.67 h / Ambient temperature

8: 90 percent / dimethylsulfoxide / 3 h / 70 °C

9: 93 percent / tetrabutylammonium fluoride / tetrahydrofuran / 18 h

10: 1.) KH / 1.) THF, 1 h, 2.) 5 h

With lead(IV) acetate; Celite; tetrabutyl ammonium fluoride; hydrogen; tert.-butyl lithium; potassium hydride; diisobutylaluminium hydride; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; toluene; benzene;

DOI:10.1021/jo00260a016

Reference yield:

(S)-[(3aR,5R,6R,6aR)-6-(tert-Butyl-diphenyl-silanyloxy)-2,2,6-trimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-hydroxy-acetaldehyde → (Z)-7-((3aR,5R,6R,6aR)-6-Benzyloxy-2,2,6-trimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-4-methyl-hept-4-enenitrile (116726-65-9)

Guidance literature:

Multi-step reaction with 9 steps

1: 88 percent / tetrahydrofuran / 3 h

2: 96 percent / H₂ / 5percent Pd/C / methanol / 3 h

3: 79 percent / DIBAL / toluene / 1 h / -78 °C

4: 1.) tert-BuLi / 1.) pentane, ether, -65 deg C, 30 min, 2.) 30 min

6: 100 percent / triethylamine / CH₂Cl₂ / 0.67 h / Ambient temperature

7: 90 percent / dimethylsulfoxide / 3 h / 70 °C

8: 93 percent / tetrabutylammonium fluoride / tetrahydrofuran / 18 h

9: 1.) KH / 1.) THF, 1 h, 2.) 5 h

With tetrabutyl ammonium fluoride; hydrogen; tert.-butyl lithium; potassium hydride; diisobutylaluminium hydride; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; toluene;

DOI:10.1021/jo00260a016

upstream raw materials:

benzyl bromide

(Z)-7-((3aR,5R,6R,6aR)-6-Hydroxy-2,2,6-trimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-4-methyl-hept-4-enenitrile

1,2;5,6-di-O-isopropylidene-3-C-methyl-α-D-allofuranose

3-[(3aR,5R,6R,6aR)-6-(tert-Butyl-diphenyl-silanyloxy)-2,2,6-trimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-propionaldehyde

Post a RFQ

Cas No.:

Product Name:

Quantity:

Please select Metric Ton KG G Pound L ML

Email:

Company name:

Valid Period:

Detailed Requirements:

• Sample
• MOQ
• GMP
• FDA
• Price
  FOB CIF CFR EXW
• Urgent purchase

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

Remove

Submit

1

What can I do for you?
Get Best Price

Get Best Price for 116726-65-9 (Z)-7-((3aR,5R,6R,6aR)-6-Benzyloxy-2,2,6-trimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-4-methyl-hept-4-enenitrile

Send

Send

Metric Ton KG G Pound L ML

Send

Send