(4aS,5R,6S,7R,8R,8aR)-6,7-bis(benzyloxy)-5,8,8a-trihydroxy-8-propyl-4a,5,6,7,8,8a-hexahydronaphthalen-1(4H)-one

Base Information

Chemical Name:(4aS,5R,6S,7R,8R,8aR)-6,7-bis(benzyloxy)-5,8,8a-trihydroxy-8-propyl-4a,5,6,7,8,8a-hexahydronaphthalen-1(4H)-one
CAS No.:1353669-90-5
Molecular Formula:C₂₇H₃₂O₆
Molecular Weight:452.547
Hs Code.:

Synonyms:(4aS,5R,6S,7R,8R,8aR)-6,7-bis(benzyloxy)-5,8,8a-trihydroxy-8-propyl-4a,5,6,7,8,8a-hexahydronaphthalen-1(4H)-one

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Chemical Property of (4aS,5R,6S,7R,8R,8aR)-6,7-bis(benzyloxy)-5,8,8a-trihydroxy-8-propyl-4a,5,6,7,8,8a-hexahydronaphthalen-1(4H)-one

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Technology Process of (4aS,5R,6S,7R,8R,8aR)-6,7-bis(benzyloxy)-5,8,8a-trihydroxy-8-propyl-4a,5,6,7,8,8a-hexahydronaphthalen-1(4H)-one

There total 8 articles about (4aS,5R,6S,7R,8R,8aR)-6,7-bis(benzyloxy)-5,8,8a-trihydroxy-8-propyl-4a,5,6,7,8,8a-hexahydronaphthalen-1(4H)-one 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: 75.0%

: 1353669-99-4
(4aS,5R,6R,7R,8R,8aR)-6,7-bis(benzyloxy)-5-[(tert-butyldimethylsilyl)oxy]-8,8a-dihydroxy-8-propyloctahydronaphthalen-1(2H)-one

: 1353669-90-5
(4aS,5R,6S,7R,8R,8aR)-6,7-bis(benzyloxy)-5,8,8a-trihydroxy-8-propyl-4a,5,6,7,8,8a-hexahydronaphthalen-1(4H)-one

Guidance literature:: (4aS,5R,6R,7R,8R,8aR)-6,7-bis(benzyloxy)-5-[(tert-butyldimethylsilyl)oxy]-8,8a-dihydroxy-8-propyloctahydronaphthalen-1(2H)-one; With Phenylselenyl chloride; boron trifluoride diethyl etherate; In dichloromethane; at 20 ℃; for 6h; Inert atmosphere;

With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; for 0.333333h; Inert atmosphere;
DOI:10.1002/ejoc.201100815

Reference yield:

: 1018784-63-8
C₂₈H₃₂O₅

: 1353669-90-5
(4aS,5R,6S,7R,8R,8aR)-6,7-bis(benzyloxy)-5,8,8a-trihydroxy-8-propyl-4a,5,6,7,8,8a-hexahydronaphthalen-1(4H)-one

Guidance literature:: Multi-step reaction with 8 steps

1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / 80 °C / Inert atmosphere

2.1: diisobutylaluminium hydride / hexane; dichloromethane / -78 °C / Inert atmosphere

2.2: Inert atmosphere

3.1: [bis(acetoxy)iodo]benzene; iodine / cyclohexane / Inert atmosphere

4.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / benzene / Inert atmosphere; Reflux

5.1: potassium carbonate / methanol; dichloromethane / 0 °C / Inert atmosphere

6.1: 1H-imidazole; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide / Inert atmosphere

7.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone; tert-butyl alcohol / 24 h / 0 °C / Inert atmosphere

8.1: Phenylselenyl chloride; boron trifluoride diethyl etherate / dichloromethane / 6 h / 20 °C / Inert atmosphere

8.2: 0.33 h / Inert atmosphere

With 1H-imidazole; osmium(VIII) oxide; Phenylselenyl chloride; 2,2'-azobis(isobutyronitrile); [bis(acetoxy)iodo]benzene; boron trifluoride diethyl etherate; iodine; tri-n-butyl-tin hydride; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; potassium carbonate; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; hexane; dichloromethane; cyclohexane; water; N,N-dimethyl-formamide; acetone; tert-butyl alcohol; benzene;
DOI:10.1002/ejoc.201100815

Reference yield:

: 1367876-75-2
C₂₈H₃₂O₅

: 1353669-90-5
(4aS,5R,6S,7R,8R,8aR)-6,7-bis(benzyloxy)-5,8,8a-trihydroxy-8-propyl-4a,5,6,7,8,8a-hexahydronaphthalen-1(4H)-one

Guidance literature:: Multi-step reaction with 7 steps

1.1: diisobutylaluminium hydride / hexane; dichloromethane / -78 °C / Inert atmosphere

1.2: Inert atmosphere

2.1: [bis(acetoxy)iodo]benzene; iodine / cyclohexane / Inert atmosphere

3.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / benzene / Inert atmosphere; Reflux

4.1: potassium carbonate / methanol; dichloromethane / 0 °C / Inert atmosphere

5.1: 1H-imidazole; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide / Inert atmosphere

6.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone; tert-butyl alcohol / 24 h / 0 °C / Inert atmosphere

7.1: Phenylselenyl chloride; boron trifluoride diethyl etherate / dichloromethane / 6 h / 20 °C / Inert atmosphere

7.2: 0.33 h / Inert atmosphere

With 1H-imidazole; osmium(VIII) oxide; Phenylselenyl chloride; 2,2'-azobis(isobutyronitrile); [bis(acetoxy)iodo]benzene; boron trifluoride diethyl etherate; iodine; tri-n-butyl-tin hydride; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; potassium carbonate; 4-methylmorpholine N-oxide; In methanol; hexane; dichloromethane; cyclohexane; water; N,N-dimethyl-formamide; acetone; tert-butyl alcohol; benzene;
DOI:10.1002/ejoc.201100815