(E)-4-Benzyl-7-[(3aS,5S,6aR)-2-hydroxy-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-4-yl]-5-(tetrahydro-pyran-2-yloxy)-hept-6-enenitrile

Base Information

Chemical Name:(E)-4-Benzyl-7-[(3aS,5S,6aR)-2-hydroxy-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-4-yl]-5-(tetrahydro-pyran-2-yloxy)-hept-6-enenitrile
CAS No.:81266-84-4
Molecular Formula:C₃₁H₄₃NO₆
Molecular Weight:525.686
Hs Code.:

Synonyms:(E)-4-Benzyl-7-[(3aS,5S,6aR)-2-hydroxy-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-4-yl]-5-(tetrahydro-pyran-2-yloxy)-hept-6-enenitrile

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Chemical Property of (E)-4-Benzyl-7-[(3aS,5S,6aR)-2-hydroxy-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-4-yl]-5-(tetrahydro-pyran-2-yloxy)-hept-6-enenitrile

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Technology Process of (E)-4-Benzyl-7-[(3aS,5S,6aR)-2-hydroxy-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-4-yl]-5-(tetrahydro-pyran-2-yloxy)-hept-6-enenitrile

There total 7 articles about (E)-4-Benzyl-7-[(3aS,5S,6aR)-2-hydroxy-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-4-yl]-5-(tetrahydro-pyran-2-yloxy)-hept-6-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: 100.0%

: 81266-82-2
4-Benzyl-5-(2-tetrahydropyranyloxy)-7-<3-oxo-7-(2-tetrahydropyranyloxy)-2-oxa-6-bicyclo<3.3.0>octyl>-6-heptennitril

: 81266-84-4
(E)-4-Benzyl-7-[(3aS,5S,6aR)-2-hydroxy-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-4-yl]-5-(tetrahydro-pyran-2-yloxy)-hept-6-enenitrile

Guidance literature:: With sodium bis(2-methoxyethoxy)aluminium dihydride; In toluene; at -70 ℃; for 6h;
DOI:10.1002/jlac.198219820116

Reference yield:

: 81266-69-5
2-Benzyl-4-cyano-butyric acid methyl ester

: 81266-84-4
(E)-4-Benzyl-7-[(3aS,5S,6aR)-2-hydroxy-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-4-yl]-5-(tetrahydro-pyran-2-yloxy)-hept-6-enenitrile

Guidance literature:: Multi-step reaction with 6 steps

1: 1) 1,6 M BuLi / 1) THF, hexane, -78 deg C, 2) 7h, -78 deg C, 2h, 20 deg C

2: 1) 2,2 M BuLi / 1) THF, hexane, 2) 1,2-dimethoxyethane, 1h, 25 deg C

3: 98 percent / ZnCl₂, NaBH₄, / 1,2-dimethoxy-ethane / 1) 1,5 h, -20 deg C, 2) 1,5 h, 0 deg C, 3) 1,5 h, 20 deg C

4: 72 percent / K₂CO₃ / ethanol / 1.5 h / 25 °C

5: 90 percent / 2percent 4-toluoene sulfonic acid / CH₂Cl₂; tetrahydrofuran / 2 h / 20 °C

6: 100 percent / 70percent Na-dihydridobis(2-methoxyethoxy)aluminat / toluene / 6 h / -70 °C

With sodium tetrahydroborate; n-butyllithium; potassium carbonate; toluene-4-sulfonic acid; sodium bis(2-methoxyethoxy)aluminium dihydride; zinc(II) chloride; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; dichloromethane; toluene;
DOI:10.1002/jlac.198219820116

Reference yield:

: 81266-72-0
4-Benzyl-6-dimethoxyphosphoryl-5-oxohexannitril

: 81266-84-4
(E)-4-Benzyl-7-[(3aS,5S,6aR)-2-hydroxy-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-4-yl]-5-(tetrahydro-pyran-2-yloxy)-hept-6-enenitrile

Guidance literature:: Multi-step reaction with 5 steps

1: 1) 2,2 M BuLi / 1) THF, hexane, 2) 1,2-dimethoxyethane, 1h, 25 deg C

2: 98 percent / ZnCl₂, NaBH₄, / 1,2-dimethoxy-ethane / 1) 1,5 h, -20 deg C, 2) 1,5 h, 0 deg C, 3) 1,5 h, 20 deg C

3: 72 percent / K₂CO₃ / ethanol / 1.5 h / 25 °C

4: 90 percent / 2percent 4-toluoene sulfonic acid / CH₂Cl₂; tetrahydrofuran / 2 h / 20 °C

5: 100 percent / 70percent Na-dihydridobis(2-methoxyethoxy)aluminat / toluene / 6 h / -70 °C

With sodium tetrahydroborate; n-butyllithium; potassium carbonate; toluene-4-sulfonic acid; sodium bis(2-methoxyethoxy)aluminium dihydride; zinc(II) chloride; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; dichloromethane; toluene;
DOI:10.1002/jlac.198219820116