(3S,3aS,4S,5aS,7R,8S,9bR)-5a-cyano-2,3,3a,4,5,5a,6,7,8,9b-decahydro-3,4,7-trimethyl-2-oxonaphtho[1,2-b]furan-8-yl benzoate

Base Information

• Chemical Name: (3S,3aS,4S,5aS,7R,8S,9bR)-5a-cyano-2,3,3a,4,5,5a,6,7,8,9b-decahydro-3,4,7-trimethyl-2-oxonaphtho[1,2-b]furan-8-yl benzoate
• CAS No.: 1354536-39-2
• Molecular Formula: C₂₃H₂₅NO₄
• Molecular Weight: 379.456

Synonyms:(3S,3aS,4S,5aS,7R,8S,9bR)-5a-cyano-2,3,3a,4,5,5a,6,7,8,9b-decahydro-3,4,7-trimethyl-2-oxonaphtho[1,2-b]furan-8-yl benzoate

Chemical Property of (3S,3aS,4S,5aS,7R,8S,9bR)-5a-cyano-2,3,3a,4,5,5a,6,7,8,9b-decahydro-3,4,7-trimethyl-2-oxonaphtho[1,2-b]furan-8-yl benzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of (3S,3aS,4S,5aS,7R,8S,9bR)-5a-cyano-2,3,3a,4,5,5a,6,7,8,9b-decahydro-3,4,7-trimethyl-2-oxonaphtho[1,2-b]furan-8-yl benzoate

There total 12 articles about (3S,3aS,4S,5aS,7R,8S,9bR)-5a-cyano-2,3,3a,4,5,5a,6,7,8,9b-decahydro-3,4,7-trimethyl-2-oxonaphtho[1,2-b]furan-8-yl benzoate 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%

(3S,3aS,4S,5aS,7R,8S,9bR)-2,3,3a,4,5,5a,6,7,8,9b-decahydro-8-hydroxy-3,4,7-trimethyl-2-oxonaphtho[1,2-b]furan-5a-carbonitrile (1354536-38-1) + benzoic acid anhydride (93-97-0) → (3S,3aS,4S,5aS,7R,8S,9bR)-5a-cyano-2,3,3a,4,5,5a,6,7,8,9b-decahydro-3,4,7-trimethyl-2-oxonaphtho[1,2-b]furan-8-yl benzoate (1354536-39-2)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1055/s-0031-1289543

Reference yield:

(1aS,2R,3aR,5S,7aR,7bS)-3a-cyano-1a,2,3,3a,4,5,7a,7b-octahydro-2,5-dimethylnaphtho[1,2-b]oxiren-7a-yl propionate (1354536-37-0) → (3S,3aS,4S,5aS,7R,8S,9bR)-5a-cyano-2,3,3a,4,5,5a,6,7,8,9b-decahydro-3,4,7-trimethyl-2-oxonaphtho[1,2-b]furan-8-yl benzoate (1354536-39-2)

Guidance literature:

Multi-step reaction with 2 steps

1: chloro-trimethyl-silane; lithium hexamethyldisilazane / tetrahydrofuran; hexane / 16.3 h / -78 - 70 °C / Inert atmosphere

2: dmap; triethylamine / dichloromethane / 1 h / 20 °C

With dmap; chloro-trimethyl-silane; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1055/s-0031-1289543

Reference yield:

isotetraline (493-04-9) → (3S,3aS,4S,5aS,7R,8S,9bR)-5a-cyano-2,3,3a,4,5,5a,6,7,8,9b-decahydro-3,4,7-trimethyl-2-oxonaphtho[1,2-b]furan-8-yl benzoate (1354536-39-2)

Guidance literature:

Multi-step reaction with 10 steps

1: sodium acetate; peracetic acid; acetic acid / dichloromethane / 1.67 h / 0 °C / Inert atmosphere

2: dichloromethane; toluene / 0.25 h / 20 °C / Reflux; Inert atmosphere

3: bis(acetylacetonate)oxovanadium / dichloromethane; toluene / 18 h / 20 - 70 °C / Inert atmosphere

4: dichloromethane; hexane / 52.5 h / 20 - 40 °C / Inert atmosphere

5: triethylamine / dichloromethane / 15 h / 20 °C / Cooling with ice; Inert atmosphere

6: 1,8-diazabicyclo[5.4.0]undec-7-ene / 12 h / 110 °C / Inert atmosphere

7: bis(acetylacetonate)oxovanadium; tert.-butylhydroperoxide / dichloromethane; toluene / 69 h / 20 °C / Inert atmosphere

8: n-butyllithium / hexane; tetrahydrofuran / 0.17 h / 20 °C / Inert atmosphere

9: chloro-trimethyl-silane; lithium hexamethyldisilazane / hexane; tetrahydrofuran / 16 h / -78 - 70 °C / Inert atmosphere

10: triethylamine; dmap / dichloromethane / 1 h / -78 - 20 °C / Inert atmosphere

With tert.-butylhydroperoxide; peracetic acid; dmap; n-butyllithium; chloro-trimethyl-silane; bis(acetylacetonate)oxovanadium; sodium acetate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; hexane; dichloromethane; toluene; 9: |Claisen Rearrangement;

DOI:10.1039/c3ob27187k

upstream raw materials:

(1aS,2R,3aR,5S,7aR,7bS)-3a-cyano-1a,2,3,3a,4,5,7a,7b-octahydro-2,5-dimethylnaphtho[1,2-b]oxiren-7a-yl propionate

(3S,3aS,4S,5aS,7R,8S,9bR)-2,3,3a,4,5,5a,6,7,8,9b-decahydro-8-hydroxy-3,4,7-trimethyl-2-oxonaphtho[1,2-b]furan-5a-carbonitrile

benzoic acid anhydride

isotetraline

Downstream raw materials:

benzoic acid (3S,3aR,4S,5aS,7R,8S,9bR)-5a-cyano-3-hydroxy-3,4,7-trimethyl-2-oxo-2,3,3a,4,5,5a,6,7,8,9b-decahydronaphtho[1,2-b]furan-8-yl ester

(3R,3aR,4S,5aS,7R,8S,9bR)-3-bromo-5a-cyano-2,3,3a,4,5,5a,6,7,8,9b-decahydro-3,4,7-trimethyl-2-oxonaphtho[1,2-b]furan-8-yl benzoate

11β-bromo-3,3-(ethylenedioxy)eudesmano-13,6α-lactone

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