(4aS,6aS,6bR,12aR)-benzyl 14-chloro-11-cyano-2,2,6a,6b,9,9,12a-heptamethyl-10-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate

Base Information

Chemical Name:(4aS,6aS,6bR,12aR)-benzyl 14-chloro-11-cyano-2,2,6a,6b,9,9,12a-heptamethyl-10-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate
CAS No.:1415383-81-1
Molecular Formula:C₃₈H₅₀ClNO₃
Molecular Weight:604.273
Hs Code.:

(4aS,6aS,6bR,12aR)-benzyl 14-chloro-11-cyano-2,2,6a,6b,9,9,12a-heptamethyl-10-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate

Synonyms:(4aS,6aS,6bR,12aR)-benzyl 14-chloro-11-cyano-2,2,6a,6b,9,9,12a-heptamethyl-10-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate

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Chemical Property of (4aS,6aS,6bR,12aR)-benzyl 14-chloro-11-cyano-2,2,6a,6b,9,9,12a-heptamethyl-10-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate

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Technology Process of (4aS,6aS,6bR,12aR)-benzyl 14-chloro-11-cyano-2,2,6a,6b,9,9,12a-heptamethyl-10-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate

There total 7 articles about (4aS,6aS,6bR,12aR)-benzyl 14-chloro-11-cyano-2,2,6a,6b,9,9,12a-heptamethyl-10-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate 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: 67.0%

: 19158-51-1
P-toluenesulfonyl cyanide

: 1415383-80-0
(4aS,6aS,6bR,12aR)-benzyl 14-chloro-2,2,6a,6b,9,9,12a-heptamethyl-10-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate

: 1415383-81-1
(4aS,6aS,6bR,12aR)-benzyl 14-chloro-11-cyano-2,2,6a,6b,9,9,12a-heptamethyl-10-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate

Guidance literature:: (4aS,6aS,6bR,12aR)-benzyl 14-chloro-2,2,6a,6b,9,9,12a-heptamethyl-10-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate; With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; at -78 - -70 ℃; for 0.5h; Inert atmosphere;

P-toluenesulfonyl cyanide; In tetrahydrofuran; hexane; at -78 ℃; for 0.75h; Inert atmosphere;

Reference yield:

: 357953-27-6
(4aS,6aS,6bR,10S,12aR)-benzyl 10-acetoxy-2,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate

: 1415383-81-1
(4aS,6aS,6bR,12aR)-benzyl 14-chloro-11-cyano-2,2,6a,6b,9,9,12a-heptamethyl-10-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: chlorine; pyridine / 0.33 h / 0 °C

2.1: potassium hydroxide / methanol / 96 h / Reflux

3.1: Dess-Martin periodane / dichloromethane / 14 h / 20 °C

4.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 - -70 °C / Inert atmosphere

4.2: 0.75 h / -78 °C / Inert atmosphere

With pyridine; n-butyllithium; chlorine; Dess-Martin periodane; diisopropylamine; potassium hydroxide; In tetrahydrofuran; methanol; hexane; dichloromethane;

Reference yield:

: 100-39-0
benzyl bromide

: 1415383-81-1
(4aS,6aS,6bR,12aR)-benzyl 14-chloro-11-cyano-2,2,6a,6b,9,9,12a-heptamethyl-10-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

1.1: potassium carbonate / N,N-dimethyl-formamide / 15 h / 20 °C

2.1: pyridine; dmap / 0 - 20 °C / Inert atmosphere

3.1: chlorine; pyridine / 0.33 h / 0 °C

4.1: potassium hydroxide / methanol / 96 h / Reflux

5.1: Dess-Martin periodane / dichloromethane / 14 h / 20 °C

6.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 - -70 °C / Inert atmosphere

6.2: 0.75 h / -78 °C / Inert atmosphere

With pyridine; dmap; n-butyllithium; chlorine; potassium carbonate; Dess-Martin periodane; diisopropylamine; potassium hydroxide; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide;