(Z)-7-[(3aR,5R,6R,6aR)-6-(tert-Butyl-diphenyl-silanyloxy)-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-(tert-Butyl-diphenyl-silanyloxy)-2,2,6-trimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-4-methyl-hept-4-enenitrile
CAS No.:116726-63-7
Molecular Formula:C₃₂H₄₃NO₄Si
Molecular Weight:533.783
Hs Code.:

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

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

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

There total 11 articles about (Z)-7-[(3aR,5R,6R,6aR)-6-(tert-Butyl-diphenyl-silanyloxy)-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: 90.0%

: 151-50-8
potassium cyanide

: 116726-62-6
Methanesulfonic acid (Z)-6-[(3aR,5R,6R,6aR)-6-(tert-butyl-diphenyl-silanyloxy)-2,2,6-trimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-3-methyl-hex-3-enyl ester

: 116726-63-7
(Z)-7-[(3aR,5R,6R,6aR)-6-(tert-Butyl-diphenyl-silanyloxy)-2,2,6-trimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-4-methyl-hept-4-enenitrile

Guidance literature:: In dimethyl sulfoxide; at 70 ℃; for 3h;
DOI:10.1021/jo00260a016

Reference yield:

: 35784-67-9
1,2;5,6-di-O-isopropylidene-3-C-methyl-α-D-allofuranose

: 116726-63-7
(Z)-7-[(3aR,5R,6R,6aR)-6-(tert-Butyl-diphenyl-silanyloxy)-2,2,6-trimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-4-methyl-hept-4-enenitrile

Guidance literature:: Multi-step reaction with 10 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

With lead(IV) acetate; Celite; 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:

: 116726-54-6
(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

: 116726-63-7
(Z)-7-[(3aR,5R,6R,6aR)-6-(tert-Butyl-diphenyl-silanyloxy)-2,2,6-trimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-4-methyl-hept-4-enenitrile

Guidance literature:: Multi-step reaction with 8 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

With lead(IV) acetate; Celite; hydrogen; tert.-butyl lithium; diisobutylaluminium hydride; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; toluene; benzene;
DOI:10.1021/jo00260a016