(1R,3aR,4S,5R,7R,8S,8aR)-5-((tert-butyldimethylsilyl)oxy)-7-isopropyl-1,4-dimethyldecahydro-4,7-epoxyazulen-8-yl cinnamate

Base Information

Chemical Name:(1R,3aR,4S,5R,7R,8S,8aR)-5-((tert-butyldimethylsilyl)oxy)-7-isopropyl-1,4-dimethyldecahydro-4,7-epoxyazulen-8-yl cinnamate
CAS No.:1232773-29-3
Molecular Formula:C₃₀H₄₆O₄Si
Molecular Weight:498.778
Hs Code.:

Synonyms:(1R,3aR,4S,5R,7R,8S,8aR)-5-((tert-butyldimethylsilyl)oxy)-7-isopropyl-1,4-dimethyldecahydro-4,7-epoxyazulen-8-yl cinnamate

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Chemical Property of (1R,3aR,4S,5R,7R,8S,8aR)-5-((tert-butyldimethylsilyl)oxy)-7-isopropyl-1,4-dimethyldecahydro-4,7-epoxyazulen-8-yl cinnamate

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Technology Process of (1R,3aR,4S,5R,7R,8S,8aR)-5-((tert-butyldimethylsilyl)oxy)-7-isopropyl-1,4-dimethyldecahydro-4,7-epoxyazulen-8-yl cinnamate

There total 18 articles about (1R,3aR,4S,5R,7R,8S,8aR)-5-((tert-butyldimethylsilyl)oxy)-7-isopropyl-1,4-dimethyldecahydro-4,7-epoxyazulen-8-yl cinnamate 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%

: 1232773-22-6
(1R,3aR,4S,5R,7R,8S,8aR)-5-((tert-butyldimethylsilyl)oxy)-7-isopropyl-1,4-dimethyldecahydro-4,7-epoxyazulen-8-ol

: 102-92-1,17082-09-6
Cinnamoyl chloride

: 1232773-29-3
(1R,3aR,4S,5R,7R,8S,8aR)-5-((tert-butyldimethylsilyl)oxy)-7-isopropyl-1,4-dimethyldecahydro-4,7-epoxyazulen-8-yl cinnamate

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 80 ℃; for 4h; Inert atmosphere;

Reference yield:

: 1232773-24-8
(6S)-2,6-dimethyl-6-(triethylsilyloxy)oct-7-yne-2,3-diol

: 1232773-29-3
(1R,3aR,4S,5R,7R,8S,8aR)-5-((tert-butyldimethylsilyl)oxy)-7-isopropyl-1,4-dimethyldecahydro-4,7-epoxyazulen-8-yl cinnamate

Guidance literature:: Multi-step reaction with 11 steps

1.1: SiO₂-supported NaIO₄ / dichloromethane / 20 °C / Inert atmosphere

2.1: benzene / 39 h / Inert atmosphere; Reflux

3.1: (4R,5R)-Ph₂-1,3-Me₂-2-oxo-2-(CH₂)5N-1,3,2-diazaphospholidine / dichloromethane / 4 h / -78 °C / Inert atmosphere

3.2: 0.25 h / 0 °C

4.1: triethylamine / dichloromethane / 3 h / -30 - 20 °C / Inert atmosphere

5.1: 1,3‐bis[2,6‐bis(propan‐2‐yl)phenyl]‐2‐[(phenylformonitrile)aurio]‐2,3‐dihydro‐1H‐imidazol‐2‐yl hexafluorostibane / dichloromethane / 10 h / 20 °C / Molecular sieve; Inert atmosphere

6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 10 h / 0 - 20 °C / Inert atmosphere

7.1: dmap; 1H-imidazole / dichloromethane / 10 h / 20 °C / Inert atmosphere

8.1: 3,5-dimethyl-1H-pyrazole; chromium(VI) oxide / dichloromethane / 2 h / Inert atmosphere

9.1: n-butyllithium; tungsten(VI) chloride / hexane; tetrahydrofuran / 2 h / 0 - 50 °C / Inert atmosphere

10.1: hydrogen / (1,5-cyclooctadiene)(pyridine)(tricyclohexylphosphine)iridium(I) tetrakis[3,5-bis(trifluoromethyl)phenyl]borate / dichloromethane / 96 h / 60006 Torr / Inert atmosphere

11.1: dmap; triethylamine / dichloromethane / 4 h / 80 °C / Inert atmosphere

With 1H-imidazole; 3,5-dimethyl-1H-pyrazole; chromium(VI) oxide; dmap; n-butyllithium; SiO₂-supported NaIO₄; tetrabutyl ammonium fluoride; hydrogen; tungsten(VI) chloride; triethylamine; (1,5-cyclooctadiene)(pyridine)(tricyclohexylphosphine)iridium(I) tetrakis[3,5-bis(trifluoromethyl)phenyl]borate; (4R,5R)-Ph₂-1,3-Me₂-2-oxo-2-(CH₂)5N-1,3,2-diazaphospholidine; 1,3‐bis[2,6‐bis(propan‐2‐yl)phenyl]‐2‐[(phenylformonitrile)aurio]‐2,3‐dihydro‐1H‐imidazol‐2‐yl hexafluorostibane; In tetrahydrofuran; hexane; dichloromethane; benzene;

Reference yield:

: 1232773-17-9
(1S,3aR,4S,5R,7R)-7-isopropyl-1,4-dimethyl-1-((triethylsilyl)oxy)-1,2,3,3a,4,5,6,7-octahydro-4,7-epoxyazulen-5-ol

: 1232773-29-3
(1R,3aR,4S,5R,7R,8S,8aR)-5-((tert-butyldimethylsilyl)oxy)-7-isopropyl-1,4-dimethyldecahydro-4,7-epoxyazulen-8-yl cinnamate

Guidance literature:: Multi-step reaction with 6 steps

1: tetrabutyl ammonium fluoride / tetrahydrofuran / 10 h / 0 - 20 °C / Inert atmosphere

2: dmap; 1H-imidazole / dichloromethane / 10 h / 20 °C / Inert atmosphere

3: 3,5-dimethyl-1H-pyrazole; chromium(VI) oxide / dichloromethane / 2 h / Inert atmosphere

4: n-butyllithium; tungsten(VI) chloride / hexane; tetrahydrofuran / 2 h / 0 - 50 °C / Inert atmosphere

5: hydrogen / (1,5-cyclooctadiene)(pyridine)(tricyclohexylphosphine)iridium(I) tetrakis[3,5-bis(trifluoromethyl)phenyl]borate / dichloromethane / 96 h / 60006 Torr / Inert atmosphere

6: dmap; triethylamine / dichloromethane / 4 h / 80 °C / Inert atmosphere

With 1H-imidazole; 3,5-dimethyl-1H-pyrazole; chromium(VI) oxide; dmap; n-butyllithium; tetrabutyl ammonium fluoride; hydrogen; tungsten(VI) chloride; triethylamine; (1,5-cyclooctadiene)(pyridine)(tricyclohexylphosphine)iridium(I) tetrakis[3,5-bis(trifluoromethyl)phenyl]borate; In tetrahydrofuran; hexane; dichloromethane;